Transmission of axial chirality to spiro center chirality, enabling enantio-specific access to erythrinan alkaloids

Synlett

Volumn , Issue 4, 2004, Pages 619-622

  Yasui, Yoshizumi ^a   Suzuki, Keisuke ^a   Matsumoto, Takashi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Axial chirality; Biphenyl compound; Erythrinan alkaloid; Spiro center chirality

Indexed keywords

2 METHYLERYSODIENONE; ALKALOID; BIPHENYL; METHYL GROUP; SPIRO COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; ERYTHRINA; STEREOSPECIFICITY; SYNTHESIS;

EID: 1642345220     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-817754     Document Type: Article

References (38)

1. (a) Dyke, S. F.; Quessy, S. N. In The Alkaloids, Vol. 18; Rodrigo, R. G. A., Ed.; Academic Press; New York, 1981, 1.
2. (b) Tsuda, Y.; Sano, T. In The Alkaloids, Vol. 48; Cordell, G. A., Ed.; Academic Press: San Diego, 1996, 249.
3. For recent synthetic studies, see: (a) Fukumoto, H.; Esumi, T.; Ishihara, J.; Hatakeyama, S. Tetrahedron Lett. 2003, 44, 8047. (b) Shimizu, K.; Takimoto, M.; Mori, M. Org. Lett. 2003, 5, 2323. (c) Gill, C.; Greenhalgh, D. A.; Simpkins, N. S. Tetrahedron Lett. 2003, 44, 7803. (d) Chikaoka, S.; Toyao, A.; Ogasawara, M.;Tamura, O.; Ishibashi, H. J. Org. Chem. 2003, 68, 312. (e) Miranda, L. D.; Zard, S. Z. Org. Lett. 2002, 4, 1135. (f) Allin, S. M.; James, S. L.; Elsegood, M. R. J.; Martin, W. P. J. Org. Chem. 2002, 67, 9464. (g) Padwa, A.; Waterson, A. G. J. Org. Chem. 2000, 65, 235. (h) Hosoi, S.; Nagao, M.; Tsuda, Y.; Isobe, K.; Sano, T.; Ohta, T. J. Chem. Soc., Perkin Trans. 1 2000, 1505. (i) For asymmetric synthesis of erythrinan alkaloid, see: Sano, T.; Kamiko, M.; Toda, J.; Hosoi, S.; Tsuda, Y. Chem. Pharm. Bull. 1994, 42, 1375. (j) Tsuda, Y.; Hosoi, S.; Isida, K.; Sangai, M. Chem. Pharm. Bull. 1994, 42, 204. (k) Tsuda, Y.; Hosoi, S.; Katagiri, N.; Kaneko, C.; Sano, T. Chem. Pharm. Bull. 1993, 41, 2087.
4. For recent synthetic studies, see: (a) Fukumoto, H.; Esumi, T.; Ishihara, J.; Hatakeyama, S. Tetrahedron Lett. 2003, 44, 8047. (b) Shimizu, K.; Takimoto, M.; Mori, M. Org. Lett. 2003, 5, 2323. (c) Gill, C.; Greenhalgh, D. A.; Simpkins, N. S. Tetrahedron Lett. 2003, 44, 7803. (d) Chikaoka, S.; Toyao, A.; Ogasawara, M.;Tamura, O.; Ishibashi, H. J. Org. Chem. 2003, 68, 312. (e) Miranda, L. D.; Zard, S. Z. Org. Lett. 2002, 4, 1135. (f) Allin, S. M.; James, S. L.; Elsegood, M. R. J.; Martin, W. P. J. Org. Chem. 2002, 67, 9464. (g) Padwa, A.; Waterson, A. G. J. Org. Chem. 2000, 65, 235. (h) Hosoi, S.; Nagao, M.; Tsuda, Y.; Isobe, K.; Sano, T.; Ohta, T. J. Chem. Soc., Perkin Trans. 1 2000, 1505. (i) For asymmetric synthesis of erythrinan alkaloid, see: Sano, T.; Kamiko, M.; Toda, J.; Hosoi, S.; Tsuda, Y. Chem. Pharm. Bull. 1994, 42, 1375. (j) Tsuda, Y.; Hosoi, S.; Isida, K.; Sangai, M. Chem. Pharm. Bull. 1994, 42, 204. (k) Tsuda, Y.; Hosoi, S.; Katagiri, N.; Kaneko, C.; Sano, T. Chem. Pharm. Bull. 1993, 41, 2087.
5. For recent synthetic studies, see: (a) Fukumoto, H.; Esumi, T.; Ishihara, J.; Hatakeyama, S. Tetrahedron Lett. 2003, 44, 8047. (b) Shimizu, K.; Takimoto, M.; Mori, M. Org. Lett. 2003, 5, 2323. (c) Gill, C.; Greenhalgh, D. A.; Simpkins, N. S. Tetrahedron Lett. 2003, 44, 7803. (d) Chikaoka, S.; Toyao, A.; Ogasawara, M.;Tamura, O.; Ishibashi, H. J. Org. Chem. 2003, 68, 312. (e) Miranda, L. D.; Zard, S. Z. Org. Lett. 2002, 4, 1135. (f) Allin, S. M.; James, S. L.; Elsegood, M. R. J.; Martin, W. P. J. Org. Chem. 2002, 67, 9464. (g) Padwa, A.; Waterson, A. G. J. Org. Chem. 2000, 65, 235. (h) Hosoi, S.; Nagao, M.; Tsuda, Y.; Isobe, K.; Sano, T.; Ohta, T. J. Chem. Soc., Perkin Trans. 1 2000, 1505. (i) For asymmetric synthesis of erythrinan alkaloid, see: Sano, T.; Kamiko, M.; Toda, J.; Hosoi, S.; Tsuda, Y. Chem. Pharm. Bull. 1994, 42, 1375. (j) Tsuda, Y.; Hosoi, S.; Isida, K.; Sangai, M. Chem. Pharm. Bull. 1994, 42, 204. (k) Tsuda, Y.; Hosoi, S.; Katagiri, N.; Kaneko, C.; Sano, T. Chem. Pharm. Bull. 1993, 41, 2087.
6. For recent synthetic studies, see: (a) Fukumoto, H.; Esumi, T.; Ishihara, J.; Hatakeyama, S. Tetrahedron Lett. 2003, 44, 8047. (b) Shimizu, K.; Takimoto, M.; Mori, M. Org. Lett. 2003, 5, 2323. (c) Gill, C.; Greenhalgh, D. A.; Simpkins, N. S. Tetrahedron Lett. 2003, 44, 7803. (d) Chikaoka, S.; Toyao, A.; Ogasawara, M.;Tamura, O.; Ishibashi, H. J. Org. Chem. 2003, 68, 312. (e) Miranda, L. D.; Zard, S. Z. Org. Lett. 2002, 4, 1135. (f) Allin, S. M.; James, S. L.; Elsegood, M. R. J.; Martin, W. P. J. Org. Chem. 2002, 67, 9464. (g) Padwa, A.; Waterson, A. G. J. Org. Chem. 2000, 65, 235. (h) Hosoi, S.; Nagao, M.; Tsuda, Y.; Isobe, K.; Sano, T.; Ohta, T. J. Chem. Soc., Perkin Trans. 1 2000, 1505. (i) For asymmetric synthesis of erythrinan alkaloid, see: Sano, T.; Kamiko, M.; Toda, J.; Hosoi, S.; Tsuda, Y. Chem. Pharm. Bull. 1994, 42, 1375. (j) Tsuda, Y.; Hosoi, S.; Isida, K.; Sangai, M. Chem. Pharm. Bull. 1994, 42, 204. (k) Tsuda, Y.; Hosoi, S.; Katagiri, N.; Kaneko, C.; Sano, T. Chem. Pharm. Bull. 1993, 41, 2087.
7. For recent synthetic studies, see: (a) Fukumoto, H.; Esumi, T.; Ishihara, J.; Hatakeyama, S. Tetrahedron Lett. 2003, 44, 8047. (b) Shimizu, K.; Takimoto, M.; Mori, M. Org. Lett. 2003, 5, 2323. (c) Gill, C.; Greenhalgh, D. A.; Simpkins, N. S. Tetrahedron Lett. 2003, 44, 7803. (d) Chikaoka, S.; Toyao, A.; Ogasawara, M.;Tamura, O.; Ishibashi, H. J. Org. Chem. 2003, 68, 312. (e) Miranda, L. D.; Zard, S. Z. Org. Lett. 2002, 4, 1135. (f) Allin, S. M.; James, S. L.; Elsegood, M. R. J.; Martin, W. P. J. Org. Chem. 2002, 67, 9464. (g) Padwa, A.; Waterson, A. G. J. Org. Chem. 2000, 65, 235. (h) Hosoi, S.; Nagao, M.; Tsuda, Y.; Isobe, K.; Sano, T.; Ohta, T. J. Chem. Soc., Perkin Trans. 1 2000, 1505. (i) For asymmetric synthesis of erythrinan alkaloid, see: Sano, T.; Kamiko, M.; Toda, J.; Hosoi, S.; Tsuda, Y. Chem. Pharm. Bull. 1994, 42, 1375. (j) Tsuda, Y.; Hosoi, S.; Isida, K.; Sangai, M. Chem. Pharm. Bull. 1994, 42, 204. (k) Tsuda, Y.; Hosoi, S.; Katagiri, N.; Kaneko, C.; Sano, T. Chem. Pharm. Bull. 1993, 41, 2087.
8. For recent synthetic studies, see: (a) Fukumoto, H.; Esumi, T.; Ishihara, J.; Hatakeyama, S. Tetrahedron Lett. 2003, 44, 8047. (b) Shimizu, K.; Takimoto, M.; Mori, M. Org. Lett. 2003, 5, 2323. (c) Gill, C.; Greenhalgh, D. A.; Simpkins, N. S. Tetrahedron Lett. 2003, 44, 7803. (d) Chikaoka, S.; Toyao, A.; Ogasawara, M.;Tamura, O.; Ishibashi, H. J. Org. Chem. 2003, 68, 312. (e) Miranda, L. D.; Zard, S. Z. Org. Lett. 2002, 4, 1135. (f) Allin, S. M.; James, S. L.; Elsegood, M. R. J.; Martin, W. P. J. Org. Chem. 2002, 67, 9464. (g) Padwa, A.; Waterson, A. G. J. Org. Chem. 2000, 65, 235. (h) Hosoi, S.; Nagao, M.; Tsuda, Y.; Isobe, K.; Sano, T.; Ohta, T. J. Chem. Soc., Perkin Trans. 1 2000, 1505. (i) For asymmetric synthesis of erythrinan alkaloid, see: Sano, T.; Kamiko, M.; Toda, J.; Hosoi, S.; Tsuda, Y. Chem. Pharm. Bull. 1994, 42, 1375. (j) Tsuda, Y.; Hosoi, S.; Isida, K.; Sangai, M. Chem. Pharm. Bull. 1994, 42, 204. (k) Tsuda, Y.; Hosoi, S.; Katagiri, N.; Kaneko, C.; Sano, T. Chem. Pharm. Bull. 1993, 41, 2087.
9. For recent synthetic studies, see: (a) Fukumoto, H.; Esumi, T.; Ishihara, J.; Hatakeyama, S. Tetrahedron Lett. 2003, 44, 8047. (b) Shimizu, K.; Takimoto, M.; Mori, M. Org. Lett. 2003, 5, 2323. (c) Gill, C.; Greenhalgh, D. A.; Simpkins, N. S. Tetrahedron Lett. 2003, 44, 7803. (d) Chikaoka, S.; Toyao, A.; Ogasawara, M.;Tamura, O.; Ishibashi, H. J. Org. Chem. 2003, 68, 312. (e) Miranda, L. D.; Zard, S. Z. Org. Lett. 2002, 4, 1135. (f) Allin, S. M.; James, S. L.; Elsegood, M. R. J.; Martin, W. P. J. Org. Chem. 2002, 67, 9464. (g) Padwa, A.; Waterson, A. G. J. Org. Chem. 2000, 65, 235. (h) Hosoi, S.; Nagao, M.; Tsuda, Y.; Isobe, K.; Sano, T.; Ohta, T. J. Chem. Soc., Perkin Trans. 1 2000, 1505. (i) For asymmetric synthesis of erythrinan alkaloid, see: Sano, T.; Kamiko, M.; Toda, J.; Hosoi, S.; Tsuda, Y. Chem. Pharm. Bull. 1994, 42, 1375. (j) Tsuda, Y.; Hosoi, S.; Isida, K.; Sangai, M. Chem. Pharm. Bull. 1994, 42, 204. (k) Tsuda, Y.; Hosoi, S.; Katagiri, N.; Kaneko, C.; Sano, T. Chem. Pharm. Bull. 1993, 41, 2087.
10. For recent synthetic studies, see: (a) Fukumoto, H.; Esumi, T.; Ishihara, J.; Hatakeyama, S. Tetrahedron Lett. 2003, 44, 8047. (b) Shimizu, K.; Takimoto, M.; Mori, M. Org. Lett. 2003, 5, 2323. (c) Gill, C.; Greenhalgh, D. A.; Simpkins, N. S. Tetrahedron Lett. 2003, 44, 7803. (d) Chikaoka, S.; Toyao, A.; Ogasawara, M.;Tamura, O.; Ishibashi, H. J. Org. Chem. 2003, 68, 312. (e) Miranda, L. D.; Zard, S. Z. Org. Lett. 2002, 4, 1135. (f) Allin, S. M.; James, S. L.; Elsegood, M. R. J.; Martin, W. P. J. Org. Chem. 2002, 67, 9464. (g) Padwa, A.; Waterson, A. G. J. Org. Chem. 2000, 65, 235. (h) Hosoi, S.; Nagao, M.; Tsuda, Y.; Isobe, K.; Sano, T.; Ohta, T. J. Chem. Soc., Perkin Trans. 1 2000, 1505. (i) For asymmetric synthesis of erythrinan alkaloid, see: Sano, T.; Kamiko, M.; Toda, J.; Hosoi, S.; Tsuda, Y. Chem. Pharm. Bull. 1994, 42, 1375. (j) Tsuda, Y.; Hosoi, S.; Isida, K.; Sangai, M. Chem. Pharm. Bull. 1994, 42, 204. (k) Tsuda, Y.; Hosoi, S.; Katagiri, N.; Kaneko, C.; Sano, T. Chem. Pharm. Bull. 1993, 41, 2087.
11. For recent synthetic studies, see: (a) Fukumoto, H.; Esumi, T.; Ishihara, J.; Hatakeyama, S. Tetrahedron Lett. 2003, 44, 8047. (b) Shimizu, K.; Takimoto, M.; Mori, M. Org. Lett. 2003, 5, 2323. (c) Gill, C.; Greenhalgh, D. A.; Simpkins, N. S. Tetrahedron Lett. 2003, 44, 7803. (d) Chikaoka, S.; Toyao, A.; Ogasawara, M.;Tamura, O.; Ishibashi, H. J. Org. Chem. 2003, 68, 312. (e) Miranda, L. D.; Zard, S. Z. Org. Lett. 2002, 4, 1135. (f) Allin, S. M.; James, S. L.; Elsegood, M. R. J.; Martin, W. P. J. Org. Chem. 2002, 67, 9464. (g) Padwa, A.; Waterson, A. G. J. Org. Chem. 2000, 65, 235. (h) Hosoi, S.; Nagao, M.; Tsuda, Y.; Isobe, K.; Sano, T.; Ohta, T. J. Chem. Soc., Perkin Trans. 1 2000, 1505. (i) For asymmetric synthesis of erythrinan alkaloid, see: Sano, T.; Kamiko, M.; Toda, J.; Hosoi, S.; Tsuda, Y. Chem. Pharm. Bull. 1994, 42, 1375. (j) Tsuda, Y.; Hosoi, S.; Isida, K.; Sangai, M. Chem. Pharm. Bull. 1994, 42, 204. (k) Tsuda, Y.; Hosoi, S.; Katagiri, N.; Kaneko, C.; Sano, T. Chem. Pharm. Bull. 1993, 41, 2087.
12. For recent synthetic studies, see: (a) Fukumoto, H.; Esumi, T.; Ishihara, J.; Hatakeyama, S. Tetrahedron Lett. 2003, 44, 8047. (b) Shimizu, K.; Takimoto, M.; Mori, M. Org. Lett. 2003, 5, 2323. (c) Gill, C.; Greenhalgh, D. A.; Simpkins, N. S. Tetrahedron Lett. 2003, 44, 7803. (d) Chikaoka, S.; Toyao, A.; Ogasawara, M.;Tamura, O.; Ishibashi, H. J. Org. Chem. 2003, 68, 312. (e) Miranda, L. D.; Zard, S. Z. Org. Lett. 2002, 4, 1135. (f) Allin, S. M.; James, S. L.; Elsegood, M. R. J.; Martin, W. P. J. Org. Chem. 2002, 67, 9464. (g) Padwa, A.; Waterson, A. G. J. Org. Chem. 2000, 65, 235. (h) Hosoi, S.; Nagao, M.; Tsuda, Y.; Isobe, K.; Sano, T.; Ohta, T. J. Chem. Soc., Perkin Trans. 1 2000, 1505. (i) For asymmetric synthesis of erythrinan alkaloid, see: Sano, T.; Kamiko, M.; Toda, J.; Hosoi, S.; Tsuda, Y. Chem. Pharm. Bull. 1994, 42, 1375. (j) Tsuda, Y.; Hosoi, S.; Isida, K.; Sangai, M. Chem. Pharm. Bull. 1994, 42, 204. (k) Tsuda, Y.; Hosoi, S.; Katagiri, N.; Kaneko, C.; Sano, T. Chem. Pharm. Bull. 1993, 41, 2087.
13. For recent synthetic studies, see: (a) Fukumoto, H.; Esumi, T.; Ishihara, J.; Hatakeyama, S. Tetrahedron Lett. 2003, 44, 8047. (b) Shimizu, K.; Takimoto, M.; Mori, M. Org. Lett. 2003, 5, 2323. (c) Gill, C.; Greenhalgh, D. A.; Simpkins, N. S. Tetrahedron Lett. 2003, 44, 7803. (d) Chikaoka, S.; Toyao, A.; Ogasawara, M.;Tamura, O.; Ishibashi, H. J. Org. Chem. 2003, 68, 312. (e) Miranda, L. D.; Zard, S. Z. Org. Lett. 2002, 4, 1135. (f) Allin, S. M.; James, S. L.; Elsegood, M. R. J.; Martin, W. P. J. Org. Chem. 2002, 67, 9464. (g) Padwa, A.; Waterson, A. G. J. Org. Chem. 2000, 65, 235. (h) Hosoi, S.; Nagao, M.; Tsuda, Y.; Isobe, K.; Sano, T.; Ohta, T. J. Chem. Soc., Perkin Trans. 1 2000, 1505. (i) For asymmetric synthesis of erythrinan alkaloid, see: Sano, T.; Kamiko, M.; Toda, J.; Hosoi, S.; Tsuda, Y. Chem. Pharm. Bull. 1994, 42, 1375. (j) Tsuda, Y.; Hosoi, S.; Isida, K.; Sangai, M. Chem. Pharm. Bull. 1994, 42, 204. (k) Tsuda, Y.; Hosoi, S.; Katagiri, N.; Kaneko, C.; Sano, T. Chem. Pharm. Bull. 1993, 41, 2087.
14. Throughout this work, the commonly accepted erythrinan numbering is used. See: Boekelheide, V.; Prelog, V. In Progress in Organic Chemistry, Vol. 3; Cook, J. W., Ed.; Butterworths Scientific: London, 1955, Chap. 5, see also ref. 1.
15. Yasui, Y.; Koga, Y.; Suzuki, K.; Matsumoto, T. Synlett 2004, DOI: 10.1055/S-2004-817753.
16. For reviews, see: (a) Bringmann, G.; Breuning, M.; Tasler, S. Synthesis 1999, 525. (b) Gant, T. G.; Meyers, A. I. Tetrahedron 1994, 50, 2297. (c) For recent examples, see: Broutin, P.-E.; Colobert, F. Org. Lett. 2003, 5, 3281. (d) Baudoin, O.; Décor, A.; Cesario, M.; Guéritte, F. Synlett 2003, 2009. (e) See also: Anderson, J. C.; Cran, J. W.; King, N. P. Tetrahedron Lett. 2003, 44, 7771. (f) Kamikawa, K.; Sakamoto, T.; Tanaka, Y.; Uemura, M. J. Org. Chem. 2003, 68, 9356. (g) Matsumoto, T.; Konegawa, T.; Nakamura, T.; Suzuki, K. Synlett 2002, 122. (h) Shimada, T.; Cho, Y.-H.; Hayashi, T. J. Am. Chem. Soc. 2002, 124, 13396.
17. For reviews, see: (a) Bringmann, G.; Breuning, M.; Tasler, S. Synthesis 1999, 525. (b) Gant, T. G.; Meyers, A. I. Tetrahedron 1994, 50, 2297. (c) For recent examples, see: Broutin, P.-E.; Colobert, F. Org. Lett. 2003, 5, 3281. (d) Baudoin, O.; Décor, A.; Cesario, M.; Guéritte, F. Synlett 2003, 2009. (e) See also: Anderson, J. C.; Cran, J. W.; King, N. P. Tetrahedron Lett. 2003, 44, 7771. (f) Kamikawa, K.; Sakamoto, T.; Tanaka, Y.; Uemura, M. J. Org. Chem. 2003, 68, 9356. (g) Matsumoto, T.; Konegawa, T.; Nakamura, T.; Suzuki, K. Synlett 2002, 122. (h) Shimada, T.; Cho, Y.-H.; Hayashi, T. J. Am. Chem. Soc. 2002, 124, 13396.
18. For reviews, see: (a) Bringmann, G.; Breuning, M.; Tasler, S. Synthesis 1999, 525. (b) Gant, T. G.; Meyers, A. I. Tetrahedron 1994, 50, 2297. (c) For recent examples, see: Broutin, P.-E.; Colobert, F. Org. Lett. 2003, 5, 3281. (d) Baudoin, O.; Décor, A.; Cesario, M.; Guéritte, F. Synlett 2003, 2009. (e) See also: Anderson, J. C.; Cran, J. W.; King, N. P. Tetrahedron Lett. 2003, 44, 7771. (f) Kamikawa, K.; Sakamoto, T.; Tanaka, Y.; Uemura, M. J. Org. Chem. 2003, 68, 9356. (g) Matsumoto, T.; Konegawa, T.; Nakamura, T.; Suzuki, K. Synlett 2002, 122. (h) Shimada, T.; Cho, Y.-H.; Hayashi, T. J. Am. Chem. Soc. 2002, 124, 13396.
19. For reviews, see: (a) Bringmann, G.; Breuning, M.; Tasler, S. Synthesis 1999, 525. (b) Gant, T. G.; Meyers, A. I. Tetrahedron 1994, 50, 2297. (c) For recent examples, see: Broutin, P.-E.; Colobert, F. Org. Lett. 2003, 5, 3281. (d) Baudoin, O.; Décor, A.; Cesario, M.; Guéritte, F. Synlett 2003, 2009. (e) See also: Anderson, J. C.; Cran, J. W.; King, N. P. Tetrahedron Lett. 2003, 44, 7771. (f) Kamikawa, K.; Sakamoto, T.; Tanaka, Y.; Uemura, M. J. Org. Chem. 2003, 68, 9356. (g) Matsumoto, T.; Konegawa, T.; Nakamura, T.; Suzuki, K. Synlett 2002, 122. (h) Shimada, T.; Cho, Y.-H.; Hayashi, T. J. Am. Chem. Soc. 2002, 124, 13396.
20. For reviews, see: (a) Bringmann, G.; Breuning, M.; Tasler, S. Synthesis 1999, 525. (b) Gant, T. G.; Meyers, A. I. Tetrahedron 1994, 50, 2297. (c) For recent examples, see: Broutin, P.-E.; Colobert, F. Org. Lett. 2003, 5, 3281. (d) Baudoin, O.; Décor, A.; Cesario, M.; Guéritte, F. Synlett 2003, 2009. (e) See also: Anderson, J. C.; Cran, J. W.; King, N. P. Tetrahedron Lett. 2003, 44, 7771. (f) Kamikawa, K.; Sakamoto, T.; Tanaka, Y.; Uemura, M. J. Org. Chem. 2003, 68, 9356. (g) Matsumoto, T.; Konegawa, T.; Nakamura, T.; Suzuki, K. Synlett 2002, 122. (h) Shimada, T.; Cho, Y.-H.; Hayashi, T. J. Am. Chem. Soc. 2002, 124, 13396.
21. For reviews, see: (a) Bringmann, G.; Breuning, M.; Tasler, S. Synthesis 1999, 525. (b) Gant, T. G.; Meyers, A. I. Tetrahedron 1994, 50, 2297. (c) For recent examples, see: Broutin, P.-E.; Colobert, F. Org. Lett. 2003, 5, 3281. (d) Baudoin, O.; Décor, A.; Cesario, M.; Guéritte, F. Synlett 2003, 2009. (e) See also: Anderson, J. C.; Cran, J. W.; King, N. P. Tetrahedron Lett. 2003, 44, 7771. (f) Kamikawa, K.; Sakamoto, T.; Tanaka, Y.; Uemura, M. J. Org. Chem. 2003, 68, 9356. (g) Matsumoto, T.; Konegawa, T.; Nakamura, T.; Suzuki, K. Synlett 2002, 122. (h) Shimada, T.; Cho, Y.-H.; Hayashi, T. J. Am. Chem. Soc. 2002, 124, 13396.
22. For reviews, see: (a) Bringmann, G.; Breuning, M.; Tasler, S. Synthesis 1999, 525. (b) Gant, T. G.; Meyers, A. I. Tetrahedron 1994, 50, 2297. (c) For recent examples, see: Broutin, P.-E.; Colobert, F. Org. Lett. 2003, 5, 3281. (d) Baudoin, O.; Décor, A.; Cesario, M.; Guéritte, F. Synlett 2003, 2009. (e) See also: Anderson, J. C.; Cran, J. W.; King, N. P. Tetrahedron Lett. 2003, 44, 7771. (f) Kamikawa, K.; Sakamoto, T.; Tanaka, Y.; Uemura, M. J. Org. Chem. 2003, 68, 9356. (g) Matsumoto, T.; Konegawa, T.; Nakamura, T.; Suzuki, K. Synlett 2002, 122. (h) Shimada, T.; Cho, Y.-H.; Hayashi, T. J. Am. Chem. Soc. 2002, 124, 13396.
23. For reviews, see: (a) Bringmann, G.; Breuning, M.; Tasler, S. Synthesis 1999, 525. (b) Gant, T. G.; Meyers, A. I. Tetrahedron 1994, 50, 2297. (c) For recent examples, see: Broutin, P.-E.; Colobert, F. Org. Lett. 2003, 5, 3281. (d) Baudoin, O.; Décor, A.; Cesario, M.; Guéritte, F. Synlett 2003, 2009. (e) See also: Anderson, J. C.; Cran, J. W.; King, N. P. Tetrahedron Lett. 2003, 44, 7771. (f) Kamikawa, K.; Sakamoto, T.; Tanaka, Y.; Uemura, M. J. Org. Chem. 2003, 68, 9356. (g) Matsumoto, T.; Konegawa, T.; Nakamura, T.; Suzuki, K. Synlett 2002, 122. (h) Shimada, T.; Cho, Y.-H.; Hayashi, T. J. Am. Chem. Soc. 2002, 124, 13396.
24. (a) Miyaura, N.; Yanagi, T.; Suzuki, A. Synth. Commun. 1981, 11, 513.
25. (b) Watanabe, T.; Miyaura, N.; Suzuki, A. Synlett 1992, 207.
26. (c) For a review, see: Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
27. Attempts to remove the MOM group from alcohol 4 led to concomitant desilylation.
28. We converted both isomers of 6 to O-methylerysodienone(1). The absolute configuration of each intermediate was not determined. In Scheme 2 and Scheme 3, one of the enantiomers was tentatively drawn for convenience.
29. (a) Tamura, Y.; Yakura, T.; Haruta, J.; Kita, Y. J. Org. Chem. 1987, 52, 3927.
30. (b) Lewis, N.; Wallbank, P. Synthesis 1987, 1103.
31. (c) For reviews on phenolic oxidation with hypervalent iodine reagents, see: Pelter, A.; Ward, R. S. Tetrahedron 2001, 57, 273.
32. (d) Moriarty, R. M.; Prakash, O. Org. React. 2001, 57, 327.
33. (e) For a review on synthetic uses of ortho-quinone monoacetals, see: Quideau, S.; Pouységu, L. Org. Prep. Proced. Int. 1999, 31, 617.
34. The enantiomeric purity was determined by HPLC analysis. For the analytical conditions and retention times, see ref. 6.
35. 3 might have caused racemization due to the lowered rotational barrier about the C(5)-C(13) bond (Figure 2). (Equation Presented)
36. (a) Ghosal, S.; Majumdar, S. K.; Chakraborti, A. Aust. J. Chem. 1971, 24, 2733.
37. (b) Chou, C.-T.; Swenton, J. S. J. Am. Chem. Soc. 1987, 109, 6898.
38. The specific rotation of O-methylerysodienone has not been reported.