Reductive decarboxylation of bicyclic prolinic systems. A new approach to the enantioselective synthesis of the Geissman-Waiss lactone. X-ray structure determination of a key lactone intermediate

Journal of the Brazilian Chemical Society

Volumn 14, Issue 1, 2003, Pages 27-38

  Ambrósio, João Carlos L ^a   Santos, Regina Helena De A ^b   Correia, Carlos R D ^a  

^a UNIVERSITY OF CAMPINAS   (Brazil)

^b UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Decarboxylation; Geissman Waiss lactone; Pyrrolizidine alkaloids; 2+2 cycloadditions

Indexed keywords

2 BUTANONE; ALPHA AMINO ACID; CARBAMIC ACID DERIVATIVE; DICHLOROKETENE; GEISSMAN WAISS LACTONE; KETENE DERIVATIVE; LACTONE DERIVATIVE; SELENIDE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; CYCLOADDITION; DECARBOXYLATION; ENANTIOMER; ENANTIOSELECTIVITY; OXIDATION; PRECURSOR; STEREOCHEMISTRY; SYNTHESIS; X RAY ANALYSIS;

EID: 0038417032     PISSN: 01035053     EISSN: None     Source Type: Journal    
DOI: 10.1590/S0103-50532003000100006     Document Type: Article

References (55)

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9. For previous synthesis of the Geissman-Waiss lactone and some closely related analogues, see: Wee, A. G. H.; Tetrahedron Lett. 2000, 41, 9025; Ohtake, H.; Imada, Y.; Murahashi, S. I.; Bull. Chem. Soc. Jpn. 1999, 72, 2737; Miranda, P. C. M. L.; Correia, C. R. D.; Tetrahedron Lett. 1999, 40, 7735; Murahashi, S.; Ohtake, H.; Imada, Y.; Tetrahedron Lett. 1998, 39, 2765; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Perkin Trans. 1 1997, 2089; Kouyama, T.; Matsunaga, H.; Ishizuka, T.; Kunieda, T.; Heterocycles 1997, 44, 479; SanchezSancho, F.; Valverde, S.; Herradon, B.; Tetrahedron:Asymmetry 1996, 7, 3209; Cinquin, C.; Bortolussi, M., Bloch, R.; Tetrahedron:Asymmetry 1996, 7, 3327; Paolucci, C.; Venturelli, F.; Fava, A.; Tetrahedron Lett. 1995, 36, 8127; Pandey, G.; Lakshmaiah, G.; Synlett 1994, 277; Cooper, J.; Gallagher, P. T.; Knight, D. W.; J. Chem. Soc., Perkin Trans. I 1993, 1313; De Faria, A.; Mattos, C. R. R.; Correia, C. R. D.; Tetrahedron Lett. 1993, 34, 27; Tanaka, M.; Murakami, T.; Suemune, H.; Sakai, K.; Heterocycles 1992, 33, 697; Niwa, H.; Miyachi, Y.; Okamoto, O.; Uosaki, Y.; Kuroda, A.; Ishiwata, H.; Yamada, K.; Tetrahedron 1992, 48, 393; Takahata, H.; Banba, Y.; Momose, T.; Tetrahedron:Asymmetry 1991, 2, 445; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Perkin Trans. I 1991, 1615; Thaning, M.; Wistrand, L. G.; J. Org. Chem. 1990, 55, 1406; Ikota, N.; Hanaki, A.; Heterocycles 1988, 27, 2535; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Chem. Commun. 1988, 509; Niwa, H.; Okamoto, O.; Miyachi, Y.; Ousaki, Y.; Yamada, K.; J. Org. Chem. 1987, 52, 2941; and reference 2.
10. For previous synthesis of the Geissman-Waiss lactone and some closely related analogues, see: Wee, A. G. H.; Tetrahedron Lett. 2000, 41, 9025; Ohtake, H.; Imada, Y.; Murahashi, S. I.; Bull. Chem. Soc. Jpn. 1999, 72, 2737; Miranda, P. C. M. L.; Correia, C. R. D.; Tetrahedron Lett. 1999, 40, 7735; Murahashi, S.; Ohtake, H.; Imada, Y.; Tetrahedron Lett. 1998, 39, 2765; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Perkin Trans. 1 1997, 2089; Kouyama, T.; Matsunaga, H.; Ishizuka, T.; Kunieda, T.; Heterocycles 1997, 44, 479; SanchezSancho, F.; Valverde, S.; Herradon, B.; Tetrahedron:Asymmetry 1996, 7, 3209; Cinquin, C.; Bortolussi, M., Bloch, R.; Tetrahedron:Asymmetry 1996, 7, 3327; Paolucci, C.; Venturelli, F.; Fava, A.; Tetrahedron Lett. 1995, 36, 8127; Pandey, G.; Lakshmaiah, G.; Synlett 1994, 277; Cooper, J.; Gallagher, P. T.; Knight, D. W.; J. Chem. Soc., Perkin Trans. I 1993, 1313; De Faria, A.; Mattos, C. R. R.; Correia, C. R. D.; Tetrahedron Lett. 1993, 34, 27; Tanaka, M.; Murakami, T.; Suemune, H.; Sakai, K.; Heterocycles 1992, 33, 697; Niwa, H.; Miyachi, Y.; Okamoto, O.; Uosaki, Y.; Kuroda, A.; Ishiwata, H.; Yamada, K.; Tetrahedron 1992, 48, 393; Takahata, H.; Banba, Y.; Momose, T.; Tetrahedron:Asymmetry 1991, 2, 445; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Perkin Trans. I 1991, 1615; Thaning, M.; Wistrand, L. G.; J. Org. Chem. 1990, 55, 1406; Ikota, N.; Hanaki, A.; Heterocycles 1988, 27, 2535; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Chem. Commun. 1988, 509; Niwa, H.; Okamoto, O.; Miyachi, Y.; Ousaki, Y.; Yamada, K.; J. Org. Chem. 1987, 52, 2941; and reference 2.
11. For previous synthesis of the Geissman-Waiss lactone and some closely related analogues, see: Wee, A. G. H.; Tetrahedron Lett. 2000, 41, 9025; Ohtake, H.; Imada, Y.; Murahashi, S. I.; Bull. Chem. Soc. Jpn. 1999, 72, 2737; Miranda, P. C. M. L.; Correia, C. R. D.; Tetrahedron Lett. 1999, 40, 7735; Murahashi, S.; Ohtake, H.; Imada, Y.; Tetrahedron Lett. 1998, 39, 2765; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Perkin Trans. 1 1997, 2089; Kouyama, T.; Matsunaga, H.; Ishizuka, T.; Kunieda, T.; Heterocycles 1997, 44, 479; SanchezSancho, F.; Valverde, S.; Herradon, B.; Tetrahedron:Asymmetry 1996, 7, 3209; Cinquin, C.; Bortolussi, M., Bloch, R.; Tetrahedron:Asymmetry 1996, 7, 3327; Paolucci, C.; Venturelli, F.; Fava, A.; Tetrahedron Lett. 1995, 36, 8127; Pandey, G.; Lakshmaiah, G.; Synlett 1994, 277; Cooper, J.; Gallagher, P. T.; Knight, D. W.; J. Chem. Soc., Perkin Trans. I 1993, 1313; De Faria, A.; Mattos, C. R. R.; Correia, C. R. D.; Tetrahedron Lett. 1993, 34, 27; Tanaka, M.; Murakami, T.; Suemune, H.; Sakai, K.; Heterocycles 1992, 33, 697; Niwa, H.; Miyachi, Y.; Okamoto, O.; Uosaki, Y.; Kuroda, A.; Ishiwata, H.; Yamada, K.; Tetrahedron 1992, 48, 393; Takahata, H.; Banba, Y.; Momose, T.; Tetrahedron:Asymmetry 1991, 2, 445; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Perkin Trans. I 1991, 1615; Thaning, M.; Wistrand, L. G.; J. Org. Chem. 1990, 55, 1406; Ikota, N.; Hanaki, A.; Heterocycles 1988, 27, 2535; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Chem. Commun. 1988, 509; Niwa, H.; Okamoto, O.; Miyachi, Y.; Ousaki, Y.; Yamada, K.; J. Org. Chem. 1987, 52, 2941; and reference 2.
12. For previous synthesis of the Geissman-Waiss lactone and some closely related analogues, see: Wee, A. G. H.; Tetrahedron Lett. 2000, 41, 9025; Ohtake, H.; Imada, Y.; Murahashi, S. I.; Bull. Chem. Soc. Jpn. 1999, 72, 2737; Miranda, P. C. M. L.; Correia, C. R. D.; Tetrahedron Lett. 1999, 40, 7735; Murahashi, S.; Ohtake, H.; Imada, Y.; Tetrahedron Lett. 1998, 39, 2765; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Perkin Trans. 1 1997, 2089; Kouyama, T.; Matsunaga, H.; Ishizuka, T.; Kunieda, T.; Heterocycles 1997, 44, 479; SanchezSancho, F.; Valverde, S.; Herradon, B.; Tetrahedron:Asymmetry 1996, 7, 3209; Cinquin, C.; Bortolussi, M., Bloch, R.; Tetrahedron:Asymmetry 1996, 7, 3327; Paolucci, C.; Venturelli, F.; Fava, A.; Tetrahedron Lett. 1995, 36, 8127; Pandey, G.; Lakshmaiah, G.; Synlett 1994, 277; Cooper, J.; Gallagher, P. T.; Knight, D. W.; J. Chem. Soc., Perkin Trans. I 1993, 1313; De Faria, A.; Mattos, C. R. R.; Correia, C. R. D.; Tetrahedron Lett. 1993, 34, 27; Tanaka, M.; Murakami, T.; Suemune, H.; Sakai, K.; Heterocycles 1992, 33, 697; Niwa, H.; Miyachi, Y.; Okamoto, O.; Uosaki, Y.; Kuroda, A.; Ishiwata, H.; Yamada, K.; Tetrahedron 1992, 48, 393; Takahata, H.; Banba, Y.; Momose, T.; Tetrahedron:Asymmetry 1991, 2, 445; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Perkin Trans. I 1991, 1615; Thaning, M.; Wistrand, L. G.; J. Org. Chem. 1990, 55, 1406; Ikota, N.; Hanaki, A.; Heterocycles 1988, 27, 2535; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Chem. Commun. 1988, 509; Niwa, H.; Okamoto, O.; Miyachi, Y.; Ousaki, Y.; Yamada, K.; J. Org. Chem. 1987, 52, 2941; and reference 2.
13. For previous synthesis of the Geissman-Waiss lactone and some closely related analogues, see: Wee, A. G. H.; Tetrahedron Lett. 2000, 41, 9025; Ohtake, H.; Imada, Y.; Murahashi, S. I.; Bull. Chem. Soc. Jpn. 1999, 72, 2737; Miranda, P. C. M. L.; Correia, C. R. D.; Tetrahedron Lett. 1999, 40, 7735; Murahashi, S.; Ohtake, H.; Imada, Y.; Tetrahedron Lett. 1998, 39, 2765; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Perkin Trans. 1 1997, 2089; Kouyama, T.; Matsunaga, H.; Ishizuka, T.; Kunieda, T.; Heterocycles 1997, 44, 479; SanchezSancho, F.; Valverde, S.; Herradon, B.; Tetrahedron:Asymmetry 1996, 7, 3209; Cinquin, C.; Bortolussi, M., Bloch, R.; Tetrahedron:Asymmetry 1996, 7, 3327; Paolucci, C.; Venturelli, F.; Fava, A.; Tetrahedron Lett. 1995, 36, 8127; Pandey, G.; Lakshmaiah, G.; Synlett 1994, 277; Cooper, J.; Gallagher, P. T.; Knight, D. W.; J. Chem. Soc., Perkin Trans. I 1993, 1313; De Faria, A.; Mattos, C. R. R.; Correia, C. R. D.; Tetrahedron Lett. 1993, 34, 27; Tanaka, M.; Murakami, T.; Suemune, H.; Sakai, K.; Heterocycles 1992, 33, 697; Niwa, H.; Miyachi, Y.; Okamoto, O.; Uosaki, Y.; Kuroda, A.; Ishiwata, H.; Yamada, K.; Tetrahedron 1992, 48, 393; Takahata, H.; Banba, Y.; Momose, T.; Tetrahedron:Asymmetry 1991, 2, 445; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Perkin Trans. I 1991, 1615; Thaning, M.; Wistrand, L. G.; J. Org. Chem. 1990, 55, 1406; Ikota, N.; Hanaki, A.; Heterocycles 1988, 27, 2535; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Chem. Commun. 1988, 509; Niwa, H.; Okamoto, O.; Miyachi, Y.; Ousaki, Y.; Yamada, K.; J. Org. Chem. 1987, 52, 2941; and reference 2.
14. For previous synthesis of the Geissman-Waiss lactone and some closely related analogues, see: Wee, A. G. H.; Tetrahedron Lett. 2000, 41, 9025; Ohtake, H.; Imada, Y.; Murahashi, S. I.; Bull. Chem. Soc. Jpn. 1999, 72, 2737; Miranda, P. C. M. L.; Correia, C. R. D.; Tetrahedron Lett. 1999, 40, 7735; Murahashi, S.; Ohtake, H.; Imada, Y.; Tetrahedron Lett. 1998, 39, 2765; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Perkin Trans. 1 1997, 2089; Kouyama, T.; Matsunaga, H.; Ishizuka, T.; Kunieda, T.; Heterocycles 1997, 44, 479; SanchezSancho, F.; Valverde, S.; Herradon, B.; Tetrahedron:Asymmetry 1996, 7, 3209; Cinquin, C.; Bortolussi, M., Bloch, R.; Tetrahedron:Asymmetry 1996, 7, 3327; Paolucci, C.; Venturelli, F.; Fava, A.; Tetrahedron Lett. 1995, 36, 8127; Pandey, G.; Lakshmaiah, G.; Synlett 1994, 277; Cooper, J.; Gallagher, P. T.; Knight, D. W.; J. Chem. Soc., Perkin Trans. I 1993, 1313; De Faria, A.; Mattos, C. R. R.; Correia, C. R. D.; Tetrahedron Lett. 1993, 34, 27; Tanaka, M.; Murakami, T.; Suemune, H.; Sakai, K.; Heterocycles 1992, 33, 697; Niwa, H.; Miyachi, Y.; Okamoto, O.; Uosaki, Y.; Kuroda, A.; Ishiwata, H.; Yamada, K.; Tetrahedron 1992, 48, 393; Takahata, H.; Banba, Y.; Momose, T.; Tetrahedron:Asymmetry 1991, 2, 445; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Perkin Trans. I 1991, 1615; Thaning, M.; Wistrand, L. G.; J. Org. Chem. 1990, 55, 1406; Ikota, N.; Hanaki, A.; Heterocycles 1988, 27, 2535; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Chem. Commun. 1988, 509; Niwa, H.; Okamoto, O.; Miyachi, Y.; Ousaki, Y.; Yamada, K.; J. Org. Chem. 1987, 52, 2941; and reference 2.
15. For previous synthesis of the Geissman-Waiss lactone and some closely related analogues, see: Wee, A. G. H.; Tetrahedron Lett. 2000, 41, 9025; Ohtake, H.; Imada, Y.; Murahashi, S. I.; Bull. Chem. Soc. Jpn. 1999, 72, 2737; Miranda, P. C. M. L.; Correia, C. R. D.; Tetrahedron Lett. 1999, 40, 7735; Murahashi, S.; Ohtake, H.; Imada, Y.; Tetrahedron Lett. 1998, 39, 2765; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Perkin Trans. 1 1997, 2089; Kouyama, T.; Matsunaga, H.; Ishizuka, T.; Kunieda, T.; Heterocycles 1997, 44, 479; SanchezSancho, F.; Valverde, S.; Herradon, B.; Tetrahedron:Asymmetry 1996, 7, 3209; Cinquin, C.; Bortolussi, M., Bloch, R.; Tetrahedron:Asymmetry 1996, 7, 3327; Paolucci, C.; Venturelli, F.; Fava, A.; Tetrahedron Lett. 1995, 36, 8127; Pandey, G.; Lakshmaiah, G.; Synlett 1994, 277; Cooper, J.; Gallagher, P. T.; Knight, D. W.; J. Chem. Soc., Perkin Trans. I 1993, 1313; De Faria, A.; Mattos, C. R. R.; Correia, C. R. D.; Tetrahedron Lett. 1993, 34, 27; Tanaka, M.; Murakami, T.; Suemune, H.; Sakai, K.; Heterocycles 1992, 33, 697; Niwa, H.; Miyachi, Y.; Okamoto, O.; Uosaki, Y.; Kuroda, A.; Ishiwata, H.; Yamada, K.; Tetrahedron 1992, 48, 393; Takahata, H.; Banba, Y.; Momose, T.; Tetrahedron:Asymmetry 1991, 2, 445; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Perkin Trans. I 1991, 1615; Thaning, M.; Wistrand, L. G.; J. Org. Chem. 1990, 55, 1406; Ikota, N.; Hanaki, A.; Heterocycles 1988, 27, 2535; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Chem. Commun. 1988, 509; Niwa, H.; Okamoto, O.; Miyachi, Y.; Ousaki, Y.; Yamada, K.; J. Org. Chem. 1987, 52, 2941; and reference 2.
16. For previous synthesis of the Geissman-Waiss lactone and some closely related analogues, see: Wee, A. G. H.; Tetrahedron Lett. 2000, 41, 9025; Ohtake, H.; Imada, Y.; Murahashi, S. I.; Bull. Chem. Soc. Jpn. 1999, 72, 2737; Miranda, P. C. M. L.; Correia, C. R. D.; Tetrahedron Lett. 1999, 40, 7735; Murahashi, S.; Ohtake, H.; Imada, Y.; Tetrahedron Lett. 1998, 39, 2765; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Perkin Trans. 1 1997, 2089; Kouyama, T.; Matsunaga, H.; Ishizuka, T.; Kunieda, T.; Heterocycles 1997, 44, 479; SanchezSancho, F.; Valverde, S.; Herradon, B.; Tetrahedron:Asymmetry 1996, 7, 3209; Cinquin, C.; Bortolussi, M., Bloch, R.; Tetrahedron:Asymmetry 1996, 7, 3327; Paolucci, C.; Venturelli, F.; Fava, A.; Tetrahedron Lett. 1995, 36, 8127; Pandey, G.; Lakshmaiah, G.; Synlett 1994, 277; Cooper, J.; Gallagher, P. T.; Knight, D. W.; J. Chem. Soc., Perkin Trans. I 1993, 1313; De Faria, A.; Mattos, C. R. R.; Correia, C. R. D.; Tetrahedron Lett. 1993, 34, 27; Tanaka, M.; Murakami, T.; Suemune, H.; Sakai, K.; Heterocycles 1992, 33, 697; Niwa, H.; Miyachi, Y.; Okamoto, O.; Uosaki, Y.; Kuroda, A.; Ishiwata, H.; Yamada, K.; Tetrahedron 1992, 48, 393; Takahata, H.; Banba, Y.; Momose, T.; Tetrahedron:Asymmetry 1991, 2, 445; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Perkin Trans. I 1991, 1615; Thaning, M.; Wistrand, L. G.; J. Org. Chem. 1990, 55, 1406; Ikota, N.; Hanaki, A.; Heterocycles 1988, 27, 2535; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Chem. Commun. 1988, 509; Niwa, H.; Okamoto, O.; Miyachi, Y.; Ousaki, Y.; Yamada, K.; J. Org. Chem. 1987, 52, 2941; and reference 2.
17. For previous synthesis of the Geissman-Waiss lactone and some closely related analogues, see: Wee, A. G. H.; Tetrahedron Lett. 2000, 41, 9025; Ohtake, H.; Imada, Y.; Murahashi, S. I.; Bull. Chem. Soc. Jpn. 1999, 72, 2737; Miranda, P. C. M. L.; Correia, C. R. D.; Tetrahedron Lett. 1999, 40, 7735; Murahashi, S.; Ohtake, H.; Imada, Y.; Tetrahedron Lett. 1998, 39, 2765; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Perkin Trans. 1 1997, 2089; Kouyama, T.; Matsunaga, H.; Ishizuka, T.; Kunieda, T.; Heterocycles 1997, 44, 479; SanchezSancho, F.; Valverde, S.; Herradon, B.; Tetrahedron:Asymmetry 1996, 7, 3209; Cinquin, C.; Bortolussi, M., Bloch, R.; Tetrahedron:Asymmetry 1996, 7, 3327; Paolucci, C.; Venturelli, F.; Fava, A.; Tetrahedron Lett. 1995, 36, 8127; Pandey, G.; Lakshmaiah, G.; Synlett 1994, 277; Cooper, J.; Gallagher, P. T.; Knight, D. W.; J. Chem. Soc., Perkin Trans. I 1993, 1313; De Faria, A.; Mattos, C. R. R.; Correia, C. R. D.; Tetrahedron Lett. 1993, 34, 27; Tanaka, M.; Murakami, T.; Suemune, H.; Sakai, K.; Heterocycles 1992, 33, 697; Niwa, H.; Miyachi, Y.; Okamoto, O.; Uosaki, Y.; Kuroda, A.; Ishiwata, H.; Yamada, K.; Tetrahedron 1992, 48, 393; Takahata, H.; Banba, Y.; Momose, T.; Tetrahedron:Asymmetry 1991, 2, 445; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Perkin Trans. I 1991, 1615; Thaning, M.; Wistrand, L. G.; J. Org. Chem. 1990, 55, 1406; Ikota, N.; Hanaki, A.; Heterocycles 1988, 27, 2535; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Chem. Commun. 1988, 509; Niwa, H.; Okamoto, O.; Miyachi, Y.; Ousaki, Y.; Yamada, K.; J. Org. Chem. 1987, 52, 2941; and reference 2.
18. For previous synthesis of the Geissman-Waiss lactone and some closely related analogues, see: Wee, A. G. H.; Tetrahedron Lett. 2000, 41, 9025; Ohtake, H.; Imada, Y.; Murahashi, S. I.; Bull. Chem. Soc. Jpn. 1999, 72, 2737; Miranda, P. C. M. L.; Correia, C. R. D.; Tetrahedron Lett. 1999, 40, 7735; Murahashi, S.; Ohtake, H.; Imada, Y.; Tetrahedron Lett. 1998, 39, 2765; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Perkin Trans. 1 1997, 2089; Kouyama, T.; Matsunaga, H.; Ishizuka, T.; Kunieda, T.; Heterocycles 1997, 44, 479; SanchezSancho, F.; Valverde, S.; Herradon, B.; Tetrahedron:Asymmetry 1996, 7, 3209; Cinquin, C.; Bortolussi, M., Bloch, R.; Tetrahedron:Asymmetry 1996, 7, 3327; Paolucci, C.; Venturelli, F.; Fava, A.; Tetrahedron Lett. 1995, 36, 8127; Pandey, G.; Lakshmaiah, G.; Synlett 1994, 277; Cooper, J.; Gallagher, P. T.; Knight, D. W.; J. Chem. Soc., Perkin Trans. I 1993, 1313; De Faria, A.; Mattos, C. R. R.; Correia, C. R. D.; Tetrahedron Lett. 1993, 34, 27; Tanaka, M.; Murakami, T.; Suemune, H.; Sakai, K.; Heterocycles 1992, 33, 697; Niwa, H.; Miyachi, Y.; Okamoto, O.; Uosaki, Y.; Kuroda, A.; Ishiwata, H.; Yamada, K.; Tetrahedron 1992, 48, 393; Takahata, H.; Banba, Y.; Momose, T.; Tetrahedron:Asymmetry 1991, 2, 445; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Perkin Trans. I 1991, 1615; Thaning, M.; Wistrand, L. G.; J. Org. Chem. 1990, 55, 1406; Ikota, N.; Hanaki, A.; Heterocycles 1988, 27, 2535; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Chem. Commun. 1988, 509; Niwa, H.; Okamoto, O.; Miyachi, Y.; Ousaki, Y.; Yamada, K.; J. Org. Chem. 1987, 52, 2941; and reference 2.
19. For previous synthesis of the Geissman-Waiss lactone and some closely related analogues, see: Wee, A. G. H.; Tetrahedron Lett. 2000, 41, 9025; Ohtake, H.; Imada, Y.; Murahashi, S. I.; Bull. Chem. Soc. Jpn. 1999, 72, 2737; Miranda, P. C. M. L.; Correia, C. R. D.; Tetrahedron Lett. 1999, 40, 7735; Murahashi, S.; Ohtake, H.; Imada, Y.; Tetrahedron Lett. 1998, 39, 2765; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Perkin Trans. 1 1997, 2089; Kouyama, T.; Matsunaga, H.; Ishizuka, T.; Kunieda, T.; Heterocycles 1997, 44, 479; SanchezSancho, F.; Valverde, S.; Herradon, B.; Tetrahedron:Asymmetry 1996, 7, 3209; Cinquin, C.; Bortolussi, M., Bloch, R.; Tetrahedron:Asymmetry 1996, 7, 3327; Paolucci, C.; Venturelli, F.; Fava, A.; Tetrahedron Lett. 1995, 36, 8127; Pandey, G.; Lakshmaiah, G.; Synlett 1994, 277; Cooper, J.; Gallagher, P. T.; Knight, D. W.; J. Chem. Soc., Perkin Trans. I 1993, 1313; De Faria, A.; Mattos, C. R. R.; Correia, C. R. D.; Tetrahedron Lett. 1993, 34, 27; Tanaka, M.; Murakami, T.; Suemune, H.; Sakai, K.; Heterocycles 1992, 33, 697; Niwa, H.; Miyachi, Y.; Okamoto, O.; Uosaki, Y.; Kuroda, A.; Ishiwata, H.; Yamada, K.; Tetrahedron 1992, 48, 393; Takahata, H.; Banba, Y.; Momose, T.; Tetrahedron:Asymmetry 1991, 2, 445; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Perkin Trans. I 1991, 1615; Thaning, M.; Wistrand, L. G.; J. Org. Chem. 1990, 55, 1406; Ikota, N.; Hanaki, A.; Heterocycles 1988, 27, 2535; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Chem. Commun. 1988, 509; Niwa, H.; Okamoto, O.; Miyachi, Y.; Ousaki, Y.; Yamada, K.; J. Org. Chem. 1987, 52, 2941; and reference 2.
20. For previous synthesis of the Geissman-Waiss lactone and some closely related analogues, see: Wee, A. G. H.; Tetrahedron Lett. 2000, 41, 9025; Ohtake, H.; Imada, Y.; Murahashi, S. I.; Bull. Chem. Soc. Jpn. 1999, 72, 2737; Miranda, P. C. M. L.; Correia, C. R. D.; Tetrahedron Lett. 1999, 40, 7735; Murahashi, S.; Ohtake, H.; Imada, Y.; Tetrahedron Lett. 1998, 39, 2765; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Perkin Trans. 1 1997, 2089; Kouyama, T.; Matsunaga, H.; Ishizuka, T.; Kunieda, T.; Heterocycles 1997, 44, 479; SanchezSancho, F.; Valverde, S.; Herradon, B.; Tetrahedron:Asymmetry 1996, 7, 3209; Cinquin, C.; Bortolussi, M., Bloch, R.; Tetrahedron:Asymmetry 1996, 7, 3327; Paolucci, C.; Venturelli, F.; Fava, A.; Tetrahedron Lett. 1995, 36, 8127; Pandey, G.; Lakshmaiah, G.; Synlett 1994, 277; Cooper, J.; Gallagher, P. T.; Knight, D. W.; J. Chem. Soc., Perkin Trans. I 1993, 1313; De Faria, A.; Mattos, C. R. R.; Correia, C. R. D.; Tetrahedron Lett. 1993, 34, 27; Tanaka, M.; Murakami, T.; Suemune, H.; Sakai, K.; Heterocycles 1992, 33, 697; Niwa, H.; Miyachi, Y.; Okamoto, O.; Uosaki, Y.; Kuroda, A.; Ishiwata, H.; Yamada, K.; Tetrahedron 1992, 48, 393; Takahata, H.; Banba, Y.; Momose, T.; Tetrahedron:Asymmetry 1991, 2, 445; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Perkin Trans. I 1991, 1615; Thaning, M.; Wistrand, L. G.; J. Org. Chem. 1990, 55, 1406; Ikota, N.; Hanaki, A.; Heterocycles 1988, 27, 2535; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Chem. Commun. 1988, 509; Niwa, H.; Okamoto, O.; Miyachi, Y.; Ousaki, Y.; Yamada, K.; J. Org. Chem. 1987, 52, 2941; and reference 2.
21. For previous synthesis of the Geissman-Waiss lactone and some closely related analogues, see: Wee, A. G. H.; Tetrahedron Lett. 2000, 41, 9025; Ohtake, H.; Imada, Y.; Murahashi, S. I.; Bull. Chem. Soc. Jpn. 1999, 72, 2737; Miranda, P. C. M. L.; Correia, C. R. D.; Tetrahedron Lett. 1999, 40, 7735; Murahashi, S.; Ohtake, H.; Imada, Y.; Tetrahedron Lett. 1998, 39, 2765; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Perkin Trans. 1 1997, 2089; Kouyama, T.; Matsunaga, H.; Ishizuka, T.; Kunieda, T.; Heterocycles 1997, 44, 479; SanchezSancho, F.; Valverde, S.; Herradon, B.; Tetrahedron:Asymmetry 1996, 7, 3209; Cinquin, C.; Bortolussi, M., Bloch, R.; Tetrahedron:Asymmetry 1996, 7, 3327; Paolucci, C.; Venturelli, F.; Fava, A.; Tetrahedron Lett. 1995, 36, 8127; Pandey, G.; Lakshmaiah, G.; Synlett 1994, 277; Cooper, J.; Gallagher, P. T.; Knight, D. W.; J. Chem. Soc., Perkin Trans. I 1993, 1313; De Faria, A.; Mattos, C. R. R.; Correia, C. R. D.; Tetrahedron Lett. 1993, 34, 27; Tanaka, M.; Murakami, T.; Suemune, H.; Sakai, K.; Heterocycles 1992, 33, 697; Niwa, H.; Miyachi, Y.; Okamoto, O.; Uosaki, Y.; Kuroda, A.; Ishiwata, H.; Yamada, K.; Tetrahedron 1992, 48, 393; Takahata, H.; Banba, Y.; Momose, T.; Tetrahedron:Asymmetry 1991, 2, 445; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Perkin Trans. I 1991, 1615; Thaning, M.; Wistrand, L. G.; J. Org. Chem. 1990, 55, 1406; Ikota, N.; Hanaki, A.; Heterocycles 1988, 27, 2535; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Chem. Commun. 1988, 509; Niwa, H.; Okamoto, O.; Miyachi, Y.; Ousaki, Y.; Yamada, K.; J. Org. Chem. 1987, 52, 2941; and reference 2.
22. For previous synthesis of the Geissman-Waiss lactone and some closely related analogues, see: Wee, A. G. H.; Tetrahedron Lett. 2000, 41, 9025; Ohtake, H.; Imada, Y.; Murahashi, S. I.; Bull. Chem. Soc. Jpn. 1999, 72, 2737; Miranda, P. C. M. L.; Correia, C. R. D.; Tetrahedron Lett. 1999, 40, 7735; Murahashi, S.; Ohtake, H.; Imada, Y.; Tetrahedron Lett. 1998, 39, 2765; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Perkin Trans. 1 1997, 2089; Kouyama, T.; Matsunaga, H.; Ishizuka, T.; Kunieda, T.; Heterocycles 1997, 44, 479; SanchezSancho, F.; Valverde, S.; Herradon, B.; Tetrahedron:Asymmetry 1996, 7, 3209; Cinquin, C.; Bortolussi, M., Bloch, R.; Tetrahedron:Asymmetry 1996, 7, 3327; Paolucci, C.; Venturelli, F.; Fava, A.; Tetrahedron Lett. 1995, 36, 8127; Pandey, G.; Lakshmaiah, G.; Synlett 1994, 277; Cooper, J.; Gallagher, P. T.; Knight, D. W.; J. Chem. Soc., Perkin Trans. I 1993, 1313; De Faria, A.; Mattos, C. R. R.; Correia, C. R. D.; Tetrahedron Lett. 1993, 34, 27; Tanaka, M.; Murakami, T.; Suemune, H.; Sakai, K.; Heterocycles 1992, 33, 697; Niwa, H.; Miyachi, Y.; Okamoto, O.; Uosaki, Y.; Kuroda, A.; Ishiwata, H.; Yamada, K.; Tetrahedron 1992, 48, 393; Takahata, H.; Banba, Y.; Momose, T.; Tetrahedron:Asymmetry 1991, 2, 445; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Perkin Trans. I 1991, 1615; Thaning, M.; Wistrand, L. G.; J. Org. Chem. 1990, 55, 1406; Ikota, N.; Hanaki, A.; Heterocycles 1988, 27, 2535; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Chem. Commun. 1988, 509; Niwa, H.; Okamoto, O.; Miyachi, Y.; Ousaki, Y.; Yamada, K.; J. Org. Chem. 1987, 52, 2941; and reference 2.
23. For previous synthesis of the Geissman-Waiss lactone and some closely related analogues, see: Wee, A. G. H.; Tetrahedron Lett. 2000, 41, 9025; Ohtake, H.; Imada, Y.; Murahashi, S. I.; Bull. Chem. Soc. Jpn. 1999, 72, 2737; Miranda, P. C. M. L.; Correia, C. R. D.; Tetrahedron Lett. 1999, 40, 7735; Murahashi, S.; Ohtake, H.; Imada, Y.; Tetrahedron Lett. 1998, 39, 2765; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Perkin Trans. 1 1997, 2089; Kouyama, T.; Matsunaga, H.; Ishizuka, T.; Kunieda, T.; Heterocycles 1997, 44, 479; SanchezSancho, F.; Valverde, S.; Herradon, B.; Tetrahedron:Asymmetry 1996, 7, 3209; Cinquin, C.; Bortolussi, M., Bloch, R.; Tetrahedron:Asymmetry 1996, 7, 3327; Paolucci, C.; Venturelli, F.; Fava, A.; Tetrahedron Lett. 1995, 36, 8127; Pandey, G.; Lakshmaiah, G.; Synlett 1994, 277; Cooper, J.; Gallagher, P. T.; Knight, D. W.; J. Chem. Soc., Perkin Trans. I 1993, 1313; De Faria, A.; Mattos, C. R. R.; Correia, C. R. D.; Tetrahedron Lett. 1993, 34, 27; Tanaka, M.; Murakami, T.; Suemune, H.; Sakai, K.; Heterocycles 1992, 33, 697; Niwa, H.; Miyachi, Y.; Okamoto, O.; Uosaki, Y.; Kuroda, A.; Ishiwata, H.; Yamada, K.; Tetrahedron 1992, 48, 393; Takahata, H.; Banba, Y.; Momose, T.; Tetrahedron:Asymmetry 1991, 2, 445; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Perkin Trans. I 1991, 1615; Thaning, M.; Wistrand, L. G.; J. Org. Chem. 1990, 55, 1406; Ikota, N.; Hanaki, A.; Heterocycles 1988, 27, 2535; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Chem. Commun. 1988, 509; Niwa, H.; Okamoto, O.; Miyachi, Y.; Ousaki, Y.; Yamada, K.; J. Org. Chem. 1987, 52, 2941; and reference 2.
24. For previous synthesis of the Geissman-Waiss lactone and some closely related analogues, see: Wee, A. G. H.; Tetrahedron Lett. 2000, 41, 9025; Ohtake, H.; Imada, Y.; Murahashi, S. I.; Bull. Chem. Soc. Jpn. 1999, 72, 2737; Miranda, P. C. M. L.; Correia, C. R. D.; Tetrahedron Lett. 1999, 40, 7735; Murahashi, S.; Ohtake, H.; Imada, Y.; Tetrahedron Lett. 1998, 39, 2765; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Perkin Trans. 1 1997, 2089; Kouyama, T.; Matsunaga, H.; Ishizuka, T.; Kunieda, T.; Heterocycles 1997, 44, 479; SanchezSancho, F.; Valverde, S.; Herradon, B.; Tetrahedron:Asymmetry 1996, 7, 3209; Cinquin, C.; Bortolussi, M., Bloch, R.; Tetrahedron:Asymmetry 1996, 7, 3327; Paolucci, C.; Venturelli, F.; Fava, A.; Tetrahedron Lett. 1995, 36, 8127; Pandey, G.; Lakshmaiah, G.; Synlett 1994, 277; Cooper, J.; Gallagher, P. T.; Knight, D. W.; J. Chem. Soc., Perkin Trans. I 1993, 1313; De Faria, A.; Mattos, C. R. R.; Correia, C. R. D.; Tetrahedron Lett. 1993, 34, 27; Tanaka, M.; Murakami, T.; Suemune, H.; Sakai, K.; Heterocycles 1992, 33, 697; Niwa, H.; Miyachi, Y.; Okamoto, O.; Uosaki, Y.; Kuroda, A.; Ishiwata, H.; Yamada, K.; Tetrahedron 1992, 48, 393; Takahata, H.; Banba, Y.; Momose, T.; Tetrahedron:Asymmetry 1991, 2, 445; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Perkin Trans. I 1991, 1615; Thaning, M.; Wistrand, L. G.; J. Org. Chem. 1990, 55, 1406; Ikota, N.; Hanaki, A.; Heterocycles 1988, 27, 2535; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Chem. Commun. 1988, 509; Niwa, H.; Okamoto, O.; Miyachi, Y.; Ousaki, Y.; Yamada, K.; J. Org. Chem. 1987, 52, 2941; and reference 2.
25. For previous synthesis of the Geissman-Waiss lactone and some closely related analogues, see: Wee, A. G. H.; Tetrahedron Lett. 2000, 41, 9025; Ohtake, H.; Imada, Y.; Murahashi, S. I.; Bull. Chem. Soc. Jpn. 1999, 72, 2737; Miranda, P. C. M. L.; Correia, C. R. D.; Tetrahedron Lett. 1999, 40, 7735; Murahashi, S.; Ohtake, H.; Imada, Y.; Tetrahedron Lett. 1998, 39, 2765; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Perkin Trans. 1 1997, 2089; Kouyama, T.; Matsunaga, H.; Ishizuka, T.; Kunieda, T.; Heterocycles 1997, 44, 479; SanchezSancho, F.; Valverde, S.; Herradon, B.; Tetrahedron:Asymmetry 1996, 7, 3209; Cinquin, C.; Bortolussi, M., Bloch, R.; Tetrahedron:Asymmetry 1996, 7, 3327; Paolucci, C.; Venturelli, F.; Fava, A.; Tetrahedron Lett. 1995, 36, 8127; Pandey, G.; Lakshmaiah, G.; Synlett 1994, 277; Cooper, J.; Gallagher, P. T.; Knight, D. W.; J. Chem. Soc., Perkin Trans. I 1993, 1313; De Faria, A.; Mattos, C. R. R.; Correia, C. R. D.; Tetrahedron Lett. 1993, 34, 27; Tanaka, M.; Murakami, T.; Suemune, H.; Sakai, K.; Heterocycles 1992, 33, 697; Niwa, H.; Miyachi, Y.; Okamoto, O.; Uosaki, Y.; Kuroda, A.; Ishiwata, H.; Yamada, K.; Tetrahedron 1992, 48, 393; Takahata, H.; Banba, Y.; Momose, T.; Tetrahedron:Asymmetry 1991, 2, 445; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Perkin Trans. I 1991, 1615; Thaning, M.; Wistrand, L. G.; J. Org. Chem. 1990, 55, 1406; Ikota, N.; Hanaki, A.; Heterocycles 1988, 27, 2535; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Chem. Commun. 1988, 509; Niwa, H.; Okamoto, O.; Miyachi, Y.; Ousaki, Y.; Yamada, K.; J. Org. Chem. 1987, 52, 2941; and reference 2.
26. For previous synthesis of the Geissman-Waiss lactone and some closely related analogues, see: Wee, A. G. H.; Tetrahedron Lett. 2000, 41, 9025; Ohtake, H.; Imada, Y.; Murahashi, S. I.; Bull. Chem. Soc. Jpn. 1999, 72, 2737; Miranda, P. C. M. L.; Correia, C. R. D.; Tetrahedron Lett. 1999, 40, 7735; Murahashi, S.; Ohtake, H.; Imada, Y.; Tetrahedron Lett. 1998, 39, 2765; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Perkin Trans. 1 1997, 2089; Kouyama, T.; Matsunaga, H.; Ishizuka, T.; Kunieda, T.; Heterocycles 1997, 44, 479; SanchezSancho, F.; Valverde, S.; Herradon, B.; Tetrahedron:Asymmetry 1996, 7, 3209; Cinquin, C.; Bortolussi, M., Bloch, R.; Tetrahedron:Asymmetry 1996, 7, 3327; Paolucci, C.; Venturelli, F.; Fava, A.; Tetrahedron Lett. 1995, 36, 8127; Pandey, G.; Lakshmaiah, G.; Synlett 1994, 277; Cooper, J.; Gallagher, P. T.; Knight, D. W.; J. Chem. Soc., Perkin Trans. I 1993, 1313; De Faria, A.; Mattos, C. R. R.; Correia, C. R. D.; Tetrahedron Lett. 1993, 34, 27; Tanaka, M.; Murakami, T.; Suemune, H.; Sakai, K.; Heterocycles 1992, 33, 697; Niwa, H.; Miyachi, Y.; Okamoto, O.; Uosaki, Y.; Kuroda, A.; Ishiwata, H.; Yamada, K.; Tetrahedron 1992, 48, 393; Takahata, H.; Banba, Y.; Momose, T.; Tetrahedron:Asymmetry 1991, 2, 445; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Perkin Trans. I 1991, 1615; Thaning, M.; Wistrand, L. G.; J. Org. Chem. 1990, 55, 1406; Ikota, N.; Hanaki, A.; Heterocycles 1988, 27, 2535; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Chem. Commun. 1988, 509; Niwa, H.; Okamoto, O.; Miyachi, Y.; Ousaki, Y.; Yamada, K.; J. Org. Chem. 1987, 52, 2941; and reference 2.
27. For previous synthesis of the Geissman-Waiss lactone and some closely related analogues, see: Wee, A. G. H.; Tetrahedron Lett. 2000, 41, 9025; Ohtake, H.; Imada, Y.; Murahashi, S. I.; Bull. Chem. Soc. Jpn. 1999, 72, 2737; Miranda, P. C. M. L.; Correia, C. R. D.; Tetrahedron Lett. 1999, 40, 7735; Murahashi, S.; Ohtake, H.; Imada, Y.; Tetrahedron Lett. 1998, 39, 2765; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Perkin Trans. 1 1997, 2089; Kouyama, T.; Matsunaga, H.; Ishizuka, T.; Kunieda, T.; Heterocycles 1997, 44, 479; SanchezSancho, F.; Valverde, S.; Herradon, B.; Tetrahedron:Asymmetry 1996, 7, 3209; Cinquin, C.; Bortolussi, M., Bloch, R.; Tetrahedron:Asymmetry 1996, 7, 3327; Paolucci, C.; Venturelli, F.; Fava, A.; Tetrahedron Lett. 1995, 36, 8127; Pandey, G.; Lakshmaiah, G.; Synlett 1994, 277; Cooper, J.; Gallagher, P. T.; Knight, D. W.; J. Chem. Soc., Perkin Trans. I 1993, 1313; De Faria, A.; Mattos, C. R. R.; Correia, C. R. D.; Tetrahedron Lett. 1993, 34, 27; Tanaka, M.; Murakami, T.; Suemune, H.; Sakai, K.; Heterocycles 1992, 33, 697; Niwa, H.; Miyachi, Y.; Okamoto, O.; Uosaki, Y.; Kuroda, A.; Ishiwata, H.; Yamada, K.; Tetrahedron 1992, 48, 393; Takahata, H.; Banba, Y.; Momose, T.; Tetrahedron:Asymmetry 1991, 2, 445; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Perkin Trans. I 1991, 1615; Thaning, M.; Wistrand, L. G.; J. Org. Chem. 1990, 55, 1406; Ikota, N.; Hanaki, A.; Heterocycles 1988, 27, 2535; Knight, D. W.; Share, A. C.; Gallagher, P. T.; J. Chem. Soc., Chem. Commun. 1988, 509; Niwa, H.; Okamoto, O.; Miyachi, Y.; Ousaki, Y.; Yamada, K.; J. Org. Chem. 1987, 52, 2941; and reference 2. ??
28. Oliveira, D. F.; Miranda, P. C. M. L.; Correia, C. R. D.; J. Org. Chem. 1999, 64, 6646; Carpes, M. J. S.; Correia, C. R. D.; Synlett 2000, 1037; Oliveira, D. F.; Severino, E. A.; Correia, C. R. D.; Tetrahedron Lett. 1999, 40, 2083; Severino, E. A.; Correia, C. R. D.; Org. Lett. 2000, 2, 3039.
29. Oliveira, D. F.; Miranda, P. C. M. L.; Correia, C. R. D.; J. Org. Chem. 1999, 64, 6646; Carpes, M. J. S.; Correia, C. R. D.; Synlett 2000, 1037; Oliveira, D. F.; Severino, E. A.; Correia, C. R. D.; Tetrahedron Lett. 1999, 40, 2083; Severino, E. A.; Correia, C. R. D.; Org. Lett. 2000, 2, 3039.
30. Oliveira, D. F.; Miranda, P. C. M. L.; Correia, C. R. D.; J. Org. Chem. 1999, 64, 6646; Carpes, M. J. S.; Correia, C. R. D.; Synlett 2000, 1037; Oliveira, D. F.; Severino, E. A.; Correia, C. R. D.; Tetrahedron Lett. 1999, 40, 2083; Severino, E. A.; Correia, C. R. D.; Org. Lett. 2000, 2, 3039.
31. Oliveira, D. F.; Miranda, P. C. M. L.; Correia, C. R. D.; J. Org. Chem. 1999, 64, 6646; Carpes, M. J. S.; Correia, C. R. D.; Synlett 2000, 1037; Oliveira, D. F.; Severino, E. A.; Correia, C. R. D.; Tetrahedron Lett. 1999, 40, 2083; Severino, E. A.; Correia, C. R. D.; Org. Lett. 2000, 2, 3039.
32. For an excellent example of this strategy, see: Martin, S. F.; Chen, K. X.; Eary, C. T.; Org. Lett. 1999, 1, 79 and references cited therein.
33. For a comprehensive review on [2+2]cycloadditions, see: Tidwell, T. T.; Ketenes; John Wiley and Sons: Toronto, 1995. For other reviews, see: Hyatt, J. A.; Raynolds, P. W.; Org. React. 1994, 45, 159; Wentrup, C.; Heilmayer, W.; Kollenz, G.; Synthesis 1994, 1219; Ghosez, L.; Brynaert, J. M. In Comprehensive Organic Synthesis; Trost, B.M; Fleming, I. eds; Pergamon: New York, Vol. 5, 1991, p. 85-122; Snider, B. B.; ChemTracts-Organic Chemistry 1991, 4, 403; Tidwell, T. T.; Acc. Chem. Res. 1990, 23, 273; Ghosez, L.; O'Donnell, M. J. In Pericyclic Reactions, Marchand, A. P.; Lehr, R. E. eds; Academic Press: New York, 1977, p 79-140.
34. For a comprehensive review on [2+2]cycloadditions, see: Tidwell, T. T.; Ketenes; John Wiley and Sons: Toronto, 1995. For other reviews, see: Hyatt, J. A.; Raynolds, P. W.; Org. React. 1994, 45, 159; Wentrup, C.; Heilmayer, W.; Kollenz, G.; Synthesis 1994, 1219; Ghosez, L.; Brynaert, J. M. In Comprehensive Organic Synthesis; Trost, B.M; Fleming, I. eds; Pergamon: New York, Vol. 5, 1991, p. 85-122; Snider, B. B.; ChemTracts-Organic Chemistry 1991, 4, 403; Tidwell, T. T.; Acc. Chem. Res. 1990, 23, 273; Ghosez, L.; O'Donnell, M. J. In Pericyclic Reactions, Marchand, A. P.; Lehr, R. E. eds; Academic Press: New York, 1977, p 79-140.
35. For a comprehensive review on [2+2]cycloadditions, see: Tidwell, T. T.; Ketenes; John Wiley and Sons: Toronto, 1995. For other reviews, see: Hyatt, J. A.; Raynolds, P. W.; Org. React. 1994, 45, 159; Wentrup, C.; Heilmayer, W.; Kollenz, G.; Synthesis 1994, 1219; Ghosez, L.; Brynaert, J. M. In Comprehensive Organic Synthesis; Trost, B.M; Fleming, I. eds; Pergamon: New York, Vol. 5, 1991, p. 85-122; Snider, B. B.; ChemTracts-Organic Chemistry 1991, 4, 403; Tidwell, T. T.; Acc. Chem. Res. 1990, 23, 273; Ghosez, L.; O'Donnell, M. J. In Pericyclic Reactions, Marchand, A. P.; Lehr, R. E. eds; Academic Press: New York, 1977, p 79-140.
36. For a comprehensive review on [2+2]cycloadditions, see: Tidwell, T. T.; Ketenes; John Wiley and Sons: Toronto, 1995. For other reviews, see: Hyatt, J. A.; Raynolds, P. W.; Org. React. 1994, 45, 159; Wentrup, C.; Heilmayer, W.; Kollenz, G.; Synthesis 1994, 1219; Ghosez, L.; Brynaert, J. M. In Comprehensive Organic Synthesis; Trost, B.M; Fleming, I. eds; Pergamon: New York, Vol. 5, 1991, p. 85-122; Snider, B. B.; ChemTracts-Organic Chemistry 1991, 4, 403; Tidwell, T. T.; Acc. Chem. Res. 1990, 23, 273; Ghosez, L.; O'Donnell, M. J. In Pericyclic Reactions, Marchand, A. P.; Lehr, R. E. eds; Academic Press: New York, 1977, p 79-140.
37. For a comprehensive review on [2+2]cycloadditions, see: Tidwell, T. T.; Ketenes; John Wiley and Sons: Toronto, 1995. For other reviews, see: Hyatt, J. A.; Raynolds, P. W.; Org. React. 1994, 45, 159; Wentrup, C.; Heilmayer, W.; Kollenz, G.; Synthesis 1994, 1219; Ghosez, L.; Brynaert, J. M. In Comprehensive Organic Synthesis; Trost, B.M; Fleming, I. eds; Pergamon: New York, Vol. 5, 1991, p. 85-122; Snider, B. B.; ChemTracts-Organic Chemistry 1991, 4, 403; Tidwell, T. T.; Acc. Chem. Res. 1990, 23, 273; Ghosez, L.; O'Donnell, M. J. In Pericyclic Reactions, Marchand, A. P.; Lehr, R. E. eds; Academic Press: New York, 1977, p 79-140.
38. For a comprehensive review on [2+2]cycloadditions, see: Tidwell, T. T.; Ketenes; John Wiley and Sons: Toronto, 1995. For other reviews, see: Hyatt, J. A.; Raynolds, P. W.; Org. React. 1994, 45, 159; Wentrup, C.; Heilmayer, W.; Kollenz, G.; Synthesis 1994, 1219; Ghosez, L.; Brynaert, J. M. In Comprehensive Organic Synthesis; Trost, B.M; Fleming, I. eds; Pergamon: New York, Vol. 5, 1991, p. 85-122; Snider, B. B.; ChemTracts-Organic Chemistry 1991, 4, 403; Tidwell, T. T.; Acc. Chem. Res. 1990, 23, 273; Ghosez, L.; O'Donnell, M. J. In Pericyclic Reactions, Marchand, A. P.; Lehr, R. E. eds; Academic Press: New York, 1977, p 79-140.
39. For a comprehensive review on [2+2]cycloadditions, see: Tidwell, T. T.; Ketenes; John Wiley and Sons: Toronto, 1995. For other reviews, see: Hyatt, J. A.; Raynolds, P. W.; Org. React. 1994, 45, 159; Wentrup, C.; Heilmayer, W.; Kollenz, G.; Synthesis 1994, 1219; Ghosez, L.; Brynaert, J. M. In Comprehensive Organic Synthesis; Trost, B.M; Fleming, I. eds; Pergamon: New York, Vol. 5, 1991, p. 85-122; Snider, B. B.; ChemTracts-Organic Chemistry 1991, 4, 403; Tidwell, T. T.; Acc. Chem. Res. 1990, 23, 273; Ghosez, L.; O'Donnell, M. J. In Pericyclic Reactions, Marchand, A. P.; Lehr, R. E. eds; Academic Press: New York, 1977, p 79-140.
40. Greene, A. E.; Kanazawa, A.; Gillet, S.; Delair, P.; J. Org. Chem. 1998, 63, 4660.
41. Pearson, D. A.; Blanchette, M.; Baker, M. L.; Guindon, C. A.; Tetrahedron Lett. 1989, 30, 2739.
42. For an extensive review on the Baeyer-Villiger oxidation of cyclobutanones and other ketones, see: Krow, G. C.; Org. React. 1993, 43, 251. For an updated review on Baeyer-Villiger oxidations using transition metals, see: Strukul, G.; Angew. Chem. Int. Ed. 1998, 37, 1198.
43. For an extensive review on the Baeyer-Villiger oxidation of cyclobutanones and other ketones, see: Krow, G. C.; Org. React. 1993, 43, 251. For an updated review on Baeyer-Villiger oxidations using transition metals, see: Strukul, G.; Angew. Chem. Int. Ed. 1998, 37, 1198.
44. Although uncommon, there are some precedents for regiocontrol of the Baeyer-Villiger by steric factors. For some illustrative examples, see: Dave, V.; Stothers, J. B.; Warnhoff, E. W.; Can. J. Chem. 1984, 62, 1965; Jacobi, P. A.; Walker, D. G.; J. Am. Chem. Soc. 1981, 103, 4611.
45. Although uncommon, there are some precedents for regiocontrol of the Baeyer-Villiger by steric factors. For some illustrative examples, see: Dave, V.; Stothers, J. B.; Warnhoff, E. W.; Can. J. Chem. 1984, 62, 1965; Jacobi, P. A.; Walker, D. G.; J. Am. Chem. Soc. 1981, 103, 4611.
46. For the preparation of acyl selenides, see: Boger, D. L.; Mathvink, R. J.; J. Org. Chem. 1992, 57, 1429; Evans, P. A.; Roseman, J. D.; Garber, L. T.; J. Org. Chem. 1996, 61, 4880. For an outstanding application of the acyl selenides for decarboxylation, see ref. 5.
47. For the preparation of acyl selenides, see: Boger, D. L.; Mathvink, R. J.; J. Org. Chem. 1992, 57, 1429; Evans, P. A.; Roseman, J. D.; Garber, L. T.; J. Org. Chem. 1996, 61, 4880. For an outstanding application of the acyl selenides for decarboxylation, see ref. 5.
48. 4OH, ∼20% yield) despite its complete regioselectivity towards the lactone, having the oxygen inserted at the C5-C6 bond of the bicyclic system. Unpublished results obtained by Mary Anne Souza Lima, Ph.D Thesis, Universidade Estadual de Campinas, Brazil, 1999.
49. Yoshifuji, S.; Tanaka, K.; Kawai, T; Nitta, Y.; Chem. Pharm. Bull. 1986, 34, 3873.
50. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 183539. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: int. code + 44(1223)336-033; E-mail: deposit @ccdc.cam.ac.uk].
51. Farrugia, L. J.; J. Appl. Crystallogr., 1999, 32, 837.
52. North, A. C. T.; Phillips, D. C.; Mathews, F. S.; Acta. Crystallogr. 1968, A24, 351.
53. Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; J. Appl. Crystallogr 1993, 26, 343.
54. Sheldrick, G.M.; SHELX97 - Programs for Crystal Structure Analysis (Release 97-2), Institüt für Anorganische Chemie der Universität, Tammanstrasse 4, D-3400 Göttingen, Germany, 1998.
55. 4 (0.34 mmol) and the reaction stirred until it turned colorless.