Diastereoselective total synthesis of isocarbacyclin from L-ascorbic acid

Journal of Organic Chemistry

Volumn 69, Issue 23, 2004, Pages 8133-8135

  Ishikawa, Teruhiko ^a   Ishii, Hirokazu ^a   Shimizu, Kazuo ^a   Nakao, Hiroe ^a   Urano, Jin ^a   Kudo, Takayuki ^a   Saito, Seiki ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL ANALYSIS; COMPOSITION; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

ASCORBIC ACID; BICYCLIC KEY INTERMEDIATE; ISOCARBACYCLIN;

ORGANIC ACIDS;

1,3 DIOXOLANE DERIVATIVE; 4,4 DIALLYL 2,2 DIMETHYL 5 (TRIMETHYLSILYL)ETHYNYL 1,3 DIOXOLANE; ALLYL COMPOUND; ASCORBIC ACID; ISOCARBACYCLIN; PROSTACYCLIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; PAUSON KHAND REACTION; STEREOCHEMISTRY; SYNTHESIS;

ASCORBIC ACID; CATALYSIS; EPOPROSTENOL; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 8644292504     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048738c     Document Type: Article

References (32)

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7. For the enantioselective synthesis of 1, see: (a) Shibasaki, M.; Fukasawa, H.; Ikegami, S. Tetrahedron Lett. 1983, 24, 3497-3500. (b) Torisawa, Y.; Okabe, H.; Shibasaki, M.; Ikegami, S. Chem. Lett. 1984, 1069-1072. (c) Sodeoka, M.; Shibasaki, M. Chem. Lett. 1984, 579-582. (d) Mase, T.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1984, 25, 5087-5090. (e) Torisawa, Y.; Okabe, H.; Ikegami, S. J. Chem. Soc., Chem. Commun. 1984, 1602-1603. (f) Ogawa, Y.; Shibasaki, M. Tetrahedron Lett. 1984, 25, 1067-1070. (g) Bannai, K.; Tanaka, T.; Okamura, N.; Hazato, A.; Sugiura, S.; Manabe, K.; Tomimori, T.; Kurozumi, S. Tetrahedron Lett. 1986, 27, 6353-6356. (h) Suzuki, M.; Koyano, H.; Noyori, R. J. Org. Chem. 1987, 52, 5583-5588. (i) Mandai, T.; Matsumoto, S.; Kohama, M.; Kawata, M.; Tsuji, J.; Saito, S.; Moriwake, T. J. Org. Chem. 1990, 55, 5671-5673. (j) Suzuki, M.; Kayano, H.; Noyori, R.; Hashimoto, H.; Negishi, M.; Ichikawa, A.; Ito, S. Tetrahedron 1992, 48, 2635-2658. (k) Park, H.; Lee, Y. S.; Jung, S. H.; Shim, S. C. Synth. Commun. 1992, 22, 1445-1452. (l) Park, H.; Lee, Y. S.; Shim, S. C. Bull. Korean Chem. Soc. 1993, 14, 86-91. (m) Mikami, K.; Toshida, A. Synlett 1995, 29-31. (n) Mikami, K.; Yoshida, A.; Matsumoto, Y. Tetrahedron Lett. 1996, 37, 8515-8518. (o) Bund, J.; Gais, H.-J.; Schmitz, E.; Erdelmeier, I.; Raabe, G. Eur. J. Org. Chem. 1998, 1319-1335.
8. For the enantioselective synthesis of 1, see: (a) Shibasaki, M.; Fukasawa, H.; Ikegami, S. Tetrahedron Lett. 1983, 24, 3497-3500. (b) Torisawa, Y.; Okabe, H.; Shibasaki, M.; Ikegami, S. Chem. Lett. 1984, 1069-1072. (c) Sodeoka, M.; Shibasaki, M. Chem. Lett. 1984, 579-582. (d) Mase, T.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1984, 25, 5087-5090. (e) Torisawa, Y.; Okabe, H.; Ikegami, S. J. Chem. Soc., Chem. Commun. 1984, 1602-1603. (f) Ogawa, Y.; Shibasaki, M. Tetrahedron Lett. 1984, 25, 1067-1070. (g) Bannai, K.; Tanaka, T.; Okamura, N.; Hazato, A.; Sugiura, S.; Manabe, K.; Tomimori, T.; Kurozumi, S. Tetrahedron Lett. 1986, 27, 6353-6356. (h) Suzuki, M.; Koyano, H.; Noyori, R. J. Org. Chem. 1987, 52, 5583-5588. (i) Mandai, T.; Matsumoto, S.; Kohama, M.; Kawata, M.; Tsuji, J.; Saito, S.; Moriwake, T. J. Org. Chem. 1990, 55, 5671-5673. (j) Suzuki, M.; Kayano, H.; Noyori, R.; Hashimoto, H.; Negishi, M.; Ichikawa, A.; Ito, S. Tetrahedron 1992, 48, 2635-2658. (k) Park, H.; Lee, Y. S.; Jung, S. H.; Shim, S. C. Synth. Commun. 1992, 22, 1445-1452. (l) Park, H.; Lee, Y. S.; Shim, S. C. Bull. Korean Chem. Soc. 1993, 14, 86-91. (m) Mikami, K.; Toshida, A. Synlett 1995, 29-31. (n) Mikami, K.; Yoshida, A.; Matsumoto, Y. Tetrahedron Lett. 1996, 37, 8515-8518. (o) Bund, J.; Gais, H.-J.; Schmitz, E.; Erdelmeier, I.; Raabe, G. Eur. J. Org. Chem. 1998, 1319-1335.
9. For the enantioselective synthesis of 1, see: (a) Shibasaki, M.; Fukasawa, H.; Ikegami, S. Tetrahedron Lett. 1983, 24, 3497-3500. (b) Torisawa, Y.; Okabe, H.; Shibasaki, M.; Ikegami, S. Chem. Lett. 1984, 1069-1072. (c) Sodeoka, M.; Shibasaki, M. Chem. Lett. 1984, 579-582. (d) Mase, T.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1984, 25, 5087-5090. (e) Torisawa, Y.; Okabe, H.; Ikegami, S. J. Chem. Soc., Chem. Commun. 1984, 1602-1603. (f) Ogawa, Y.; Shibasaki, M. Tetrahedron Lett. 1984, 25, 1067-1070. (g) Bannai, K.; Tanaka, T.; Okamura, N.; Hazato, A.; Sugiura, S.; Manabe, K.; Tomimori, T.; Kurozumi, S. Tetrahedron Lett. 1986, 27, 6353-6356. (h) Suzuki, M.; Koyano, H.; Noyori, R. J. Org. Chem. 1987, 52, 5583-5588. (i) Mandai, T.; Matsumoto, S.; Kohama, M.; Kawata, M.; Tsuji, J.; Saito, S.; Moriwake, T. J. Org. Chem. 1990, 55, 5671-5673. (j) Suzuki, M.; Kayano, H.; Noyori, R.; Hashimoto, H.; Negishi, M.; Ichikawa, A.; Ito, S. Tetrahedron 1992, 48, 2635-2658. (k) Park, H.; Lee, Y. S.; Jung, S. H.; Shim, S. C. Synth. Commun. 1992, 22, 1445-1452. (l) Park, H.; Lee, Y. S.; Shim, S. C. Bull. Korean Chem. Soc. 1993, 14, 86-91. (m) Mikami, K.; Toshida, A. Synlett 1995, 29-31. (n) Mikami, K.; Yoshida, A.; Matsumoto, Y. Tetrahedron Lett. 1996, 37, 8515-8518. (o) Bund, J.; Gais, H.-J.; Schmitz, E.; Erdelmeier, I.; Raabe, G. Eur. J. Org. Chem. 1998, 1319-1335.
10. For the enantioselective synthesis of 1, see: (a) Shibasaki, M.; Fukasawa, H.; Ikegami, S. Tetrahedron Lett. 1983, 24, 3497-3500. (b) Torisawa, Y.; Okabe, H.; Shibasaki, M.; Ikegami, S. Chem. Lett. 1984, 1069-1072. (c) Sodeoka, M.; Shibasaki, M. Chem. Lett. 1984, 579-582. (d) Mase, T.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1984, 25, 5087-5090. (e) Torisawa, Y.; Okabe, H.; Ikegami, S. J. Chem. Soc., Chem. Commun. 1984, 1602-1603. (f) Ogawa, Y.; Shibasaki, M. Tetrahedron Lett. 1984, 25, 1067-1070. (g) Bannai, K.; Tanaka, T.; Okamura, N.; Hazato, A.; Sugiura, S.; Manabe, K.; Tomimori, T.; Kurozumi, S. Tetrahedron Lett. 1986, 27, 6353-6356. (h) Suzuki, M.; Koyano, H.; Noyori, R. J. Org. Chem. 1987, 52, 5583-5588. (i) Mandai, T.; Matsumoto, S.; Kohama, M.; Kawata, M.; Tsuji, J.; Saito, S.; Moriwake, T. J. Org. Chem. 1990, 55, 5671-5673. (j) Suzuki, M.; Kayano, H.; Noyori, R.; Hashimoto, H.; Negishi, M.; Ichikawa, A.; Ito, S. Tetrahedron 1992, 48, 2635-2658. (k) Park, H.; Lee, Y. S.; Jung, S. H.; Shim, S. C. Synth. Commun. 1992, 22, 1445-1452. (l) Park, H.; Lee, Y. S.; Shim, S. C. Bull. Korean Chem. Soc. 1993, 14, 86-91. (m) Mikami, K.; Toshida, A. Synlett 1995, 29-31. (n) Mikami, K.; Yoshida, A.; Matsumoto, Y. Tetrahedron Lett. 1996, 37, 8515-8518. (o) Bund, J.; Gais, H.-J.; Schmitz, E.; Erdelmeier, I.; Raabe, G. Eur. J. Org. Chem. 1998, 1319-1335.
11. For the enantioselective synthesis of 1, see: (a) Shibasaki, M.; Fukasawa, H.; Ikegami, S. Tetrahedron Lett. 1983, 24, 3497-3500. (b) Torisawa, Y.; Okabe, H.; Shibasaki, M.; Ikegami, S. Chem. Lett. 1984, 1069-1072. (c) Sodeoka, M.; Shibasaki, M. Chem. Lett. 1984, 579-582. (d) Mase, T.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1984, 25, 5087-5090. (e) Torisawa, Y.; Okabe, H.; Ikegami, S. J. Chem. Soc., Chem. Commun. 1984, 1602-1603. (f) Ogawa, Y.; Shibasaki, M. Tetrahedron Lett. 1984, 25, 1067-1070. (g) Bannai, K.; Tanaka, T.; Okamura, N.; Hazato, A.; Sugiura, S.; Manabe, K.; Tomimori, T.; Kurozumi, S. Tetrahedron Lett. 1986, 27, 6353-6356. (h) Suzuki, M.; Koyano, H.; Noyori, R. J. Org. Chem. 1987, 52, 5583-5588. (i) Mandai, T.; Matsumoto, S.; Kohama, M.; Kawata, M.; Tsuji, J.; Saito, S.; Moriwake, T. J. Org. Chem. 1990, 55, 5671-5673. (j) Suzuki, M.; Kayano, H.; Noyori, R.; Hashimoto, H.; Negishi, M.; Ichikawa, A.; Ito, S. Tetrahedron 1992, 48, 2635-2658. (k) Park, H.; Lee, Y. S.; Jung, S. H.; Shim, S. C. Synth. Commun. 1992, 22, 1445-1452. (l) Park, H.; Lee, Y. S.; Shim, S. C. Bull. Korean Chem. Soc. 1993, 14, 86-91. (m) Mikami, K.; Toshida, A. Synlett 1995, 29-31. (n) Mikami, K.; Yoshida, A.; Matsumoto, Y. Tetrahedron Lett. 1996, 37, 8515-8518. (o) Bund, J.; Gais, H.-J.; Schmitz, E.; Erdelmeier, I.; Raabe, G. Eur. J. Org. Chem. 1998, 1319-1335.
12. For the enantioselective synthesis of 1, see: (a) Shibasaki, M.; Fukasawa, H.; Ikegami, S. Tetrahedron Lett. 1983, 24, 3497-3500. (b) Torisawa, Y.; Okabe, H.; Shibasaki, M.; Ikegami, S. Chem. Lett. 1984, 1069-1072. (c) Sodeoka, M.; Shibasaki, M. Chem. Lett. 1984, 579-582. (d) Mase, T.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1984, 25, 5087-5090. (e) Torisawa, Y.; Okabe, H.; Ikegami, S. J. Chem. Soc., Chem. Commun. 1984, 1602-1603. (f) Ogawa, Y.; Shibasaki, M. Tetrahedron Lett. 1984, 25, 1067-1070. (g) Bannai, K.; Tanaka, T.; Okamura, N.; Hazato, A.; Sugiura, S.; Manabe, K.; Tomimori, T.; Kurozumi, S. Tetrahedron Lett. 1986, 27, 6353-6356. (h) Suzuki, M.; Koyano, H.; Noyori, R. J. Org. Chem. 1987, 52, 5583-5588. (i) Mandai, T.; Matsumoto, S.; Kohama, M.; Kawata, M.; Tsuji, J.; Saito, S.; Moriwake, T. J. Org. Chem. 1990, 55, 5671-5673. (j) Suzuki, M.; Kayano, H.; Noyori, R.; Hashimoto, H.; Negishi, M.; Ichikawa, A.; Ito, S. Tetrahedron 1992, 48, 2635-2658. (k) Park, H.; Lee, Y. S.; Jung, S. H.; Shim, S. C. Synth. Commun. 1992, 22, 1445-1452. (l) Park, H.; Lee, Y. S.; Shim, S. C. Bull. Korean Chem. Soc. 1993, 14, 86-91. (m) Mikami, K.; Toshida, A. Synlett 1995, 29-31. (n) Mikami, K.; Yoshida, A.; Matsumoto, Y. Tetrahedron Lett. 1996, 37, 8515-8518. (o) Bund, J.; Gais, H.-J.; Schmitz, E.; Erdelmeier, I.; Raabe, G. Eur. J. Org. Chem. 1998, 1319-1335.
13. For the enantioselective synthesis of 1, see: (a) Shibasaki, M.; Fukasawa, H.; Ikegami, S. Tetrahedron Lett. 1983, 24, 3497-3500. (b) Torisawa, Y.; Okabe, H.; Shibasaki, M.; Ikegami, S. Chem. Lett. 1984, 1069-1072. (c) Sodeoka, M.; Shibasaki, M. Chem. Lett. 1984, 579-582. (d) Mase, T.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1984, 25, 5087-5090. (e) Torisawa, Y.; Okabe, H.; Ikegami, S. J. Chem. Soc., Chem. Commun. 1984, 1602-1603. (f) Ogawa, Y.; Shibasaki, M. Tetrahedron Lett. 1984, 25, 1067-1070. (g) Bannai, K.; Tanaka, T.; Okamura, N.; Hazato, A.; Sugiura, S.; Manabe, K.; Tomimori, T.; Kurozumi, S. Tetrahedron Lett. 1986, 27, 6353-6356. (h) Suzuki, M.; Koyano, H.; Noyori, R. J. Org. Chem. 1987, 52, 5583-5588. (i) Mandai, T.; Matsumoto, S.; Kohama, M.; Kawata, M.; Tsuji, J.; Saito, S.; Moriwake, T. J. Org. Chem. 1990, 55, 5671-5673. (j) Suzuki, M.; Kayano, H.; Noyori, R.; Hashimoto, H.; Negishi, M.; Ichikawa, A.; Ito, S. Tetrahedron 1992, 48, 2635-2658. (k) Park, H.; Lee, Y. S.; Jung, S. H.; Shim, S. C. Synth. Commun. 1992, 22, 1445-1452. (l) Park, H.; Lee, Y. S.; Shim, S. C. Bull. Korean Chem. Soc. 1993, 14, 86-91. (m) Mikami, K.; Toshida, A. Synlett 1995, 29-31. (n) Mikami, K.; Yoshida, A.; Matsumoto, Y. Tetrahedron Lett. 1996, 37, 8515-8518. (o) Bund, J.; Gais, H.-J.; Schmitz, E.; Erdelmeier, I.; Raabe, G. Eur. J. Org. Chem. 1998, 1319-1335.
14. For the enantioselective synthesis of 1, see: (a) Shibasaki, M.; Fukasawa, H.; Ikegami, S. Tetrahedron Lett. 1983, 24, 3497-3500. (b) Torisawa, Y.; Okabe, H.; Shibasaki, M.; Ikegami, S. Chem. Lett. 1984, 1069-1072. (c) Sodeoka, M.; Shibasaki, M. Chem. Lett. 1984, 579-582. (d) Mase, T.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1984, 25, 5087-5090. (e) Torisawa, Y.; Okabe, H.; Ikegami, S. J. Chem. Soc., Chem. Commun. 1984, 1602-1603. (f) Ogawa, Y.; Shibasaki, M. Tetrahedron Lett. 1984, 25, 1067-1070. (g) Bannai, K.; Tanaka, T.; Okamura, N.; Hazato, A.; Sugiura, S.; Manabe, K.; Tomimori, T.; Kurozumi, S. Tetrahedron Lett. 1986, 27, 6353-6356. (h) Suzuki, M.; Koyano, H.; Noyori, R. J. Org. Chem. 1987, 52, 5583-5588. (i) Mandai, T.; Matsumoto, S.; Kohama, M.; Kawata, M.; Tsuji, J.; Saito, S.; Moriwake, T. J. Org. Chem. 1990, 55, 5671-5673. (j) Suzuki, M.; Kayano, H.; Noyori, R.; Hashimoto, H.; Negishi, M.; Ichikawa, A.; Ito, S. Tetrahedron 1992, 48, 2635-2658. (k) Park, H.; Lee, Y. S.; Jung, S. H.; Shim, S. C. Synth. Commun. 1992, 22, 1445-1452. (l) Park, H.; Lee, Y. S.; Shim, S. C. Bull. Korean Chem. Soc. 1993, 14, 86-91. (m) Mikami, K.; Toshida, A. Synlett 1995, 29-31. (n) Mikami, K.; Yoshida, A.; Matsumoto, Y. Tetrahedron Lett. 1996, 37, 8515-8518. (o) Bund, J.; Gais, H.-J.; Schmitz, E.; Erdelmeier, I.; Raabe, G. Eur. J. Org. Chem. 1998, 1319-1335.
15. For the enantioselective synthesis of 1, see: (a) Shibasaki, M.; Fukasawa, H.; Ikegami, S. Tetrahedron Lett. 1983, 24, 3497-3500. (b) Torisawa, Y.; Okabe, H.; Shibasaki, M.; Ikegami, S. Chem. Lett. 1984, 1069-1072. (c) Sodeoka, M.; Shibasaki, M. Chem. Lett. 1984, 579-582. (d) Mase, T.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1984, 25, 5087-5090. (e) Torisawa, Y.; Okabe, H.; Ikegami, S. J. Chem. Soc., Chem. Commun. 1984, 1602-1603. (f) Ogawa, Y.; Shibasaki, M. Tetrahedron Lett. 1984, 25, 1067-1070. (g) Bannai, K.; Tanaka, T.; Okamura, N.; Hazato, A.; Sugiura, S.; Manabe, K.; Tomimori, T.; Kurozumi, S. Tetrahedron Lett. 1986, 27, 6353-6356. (h) Suzuki, M.; Koyano, H.; Noyori, R. J. Org. Chem. 1987, 52, 5583-5588. (i) Mandai, T.; Matsumoto, S.; Kohama, M.; Kawata, M.; Tsuji, J.; Saito, S.; Moriwake, T. J. Org. Chem. 1990, 55, 5671-5673. (j) Suzuki, M.; Kayano, H.; Noyori, R.; Hashimoto, H.; Negishi, M.; Ichikawa, A.; Ito, S. Tetrahedron 1992, 48, 2635-2658. (k) Park, H.; Lee, Y. S.; Jung, S. H.; Shim, S. C. Synth. Commun. 1992, 22, 1445-1452. (l) Park, H.; Lee, Y. S.; Shim, S. C. Bull. Korean Chem. Soc. 1993, 14, 86-91. (m) Mikami, K.; Toshida, A. Synlett 1995, 29-31. (n) Mikami, K.; Yoshida, A.; Matsumoto, Y. Tetrahedron Lett. 1996, 37, 8515-8518. (o) Bund, J.; Gais, H.-J.; Schmitz, E.; Erdelmeier, I.; Raabe, G. Eur. J. Org. Chem. 1998, 1319-1335.
16. For the enantioselective synthesis of 1, see: (a) Shibasaki, M.; Fukasawa, H.; Ikegami, S. Tetrahedron Lett. 1983, 24, 3497-3500. (b) Torisawa, Y.; Okabe, H.; Shibasaki, M.; Ikegami, S. Chem. Lett. 1984, 1069-1072. (c) Sodeoka, M.; Shibasaki, M. Chem. Lett. 1984, 579-582. (d) Mase, T.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1984, 25, 5087-5090. (e) Torisawa, Y.; Okabe, H.; Ikegami, S. J. Chem. Soc., Chem. Commun. 1984, 1602-1603. (f) Ogawa, Y.; Shibasaki, M. Tetrahedron Lett. 1984, 25, 1067-1070. (g) Bannai, K.; Tanaka, T.; Okamura, N.; Hazato, A.; Sugiura, S.; Manabe, K.; Tomimori, T.; Kurozumi, S. Tetrahedron Lett. 1986, 27, 6353-6356. (h) Suzuki, M.; Koyano, H.; Noyori, R. J. Org. Chem. 1987, 52, 5583-5588. (i) Mandai, T.; Matsumoto, S.; Kohama, M.; Kawata, M.; Tsuji, J.; Saito, S.; Moriwake, T. J. Org. Chem. 1990, 55, 5671-5673. (j) Suzuki, M.; Kayano, H.; Noyori, R.; Hashimoto, H.; Negishi, M.; Ichikawa, A.; Ito, S. Tetrahedron 1992, 48, 2635-2658. (k) Park, H.; Lee, Y. S.; Jung, S. H.; Shim, S. C. Synth. Commun. 1992, 22, 1445-1452. (l) Park, H.; Lee, Y. S.; Shim, S. C. Bull. Korean Chem. Soc. 1993, 14, 86-91. (m) Mikami, K.; Toshida, A. Synlett 1995, 29-31. (n) Mikami, K.; Yoshida, A.; Matsumoto, Y. Tetrahedron Lett. 1996, 37, 8515-8518. (o) Bund, J.; Gais, H.-J.; Schmitz, E.; Erdelmeier, I.; Raabe, G. Eur. J. Org. Chem. 1998, 1319-1335.
17. For the enantioselective synthesis of 1, see: (a) Shibasaki, M.; Fukasawa, H.; Ikegami, S. Tetrahedron Lett. 1983, 24, 3497-3500. (b) Torisawa, Y.; Okabe, H.; Shibasaki, M.; Ikegami, S. Chem. Lett. 1984, 1069-1072. (c) Sodeoka, M.; Shibasaki, M. Chem. Lett. 1984, 579-582. (d) Mase, T.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1984, 25, 5087-5090. (e) Torisawa, Y.; Okabe, H.; Ikegami, S. J. Chem. Soc., Chem. Commun. 1984, 1602-1603. (f) Ogawa, Y.; Shibasaki, M. Tetrahedron Lett. 1984, 25, 1067-1070. (g) Bannai, K.; Tanaka, T.; Okamura, N.; Hazato, A.; Sugiura, S.; Manabe, K.; Tomimori, T.; Kurozumi, S. Tetrahedron Lett. 1986, 27, 6353-6356. (h) Suzuki, M.; Koyano, H.; Noyori, R. J. Org. Chem. 1987, 52, 5583-5588. (i) Mandai, T.; Matsumoto, S.; Kohama, M.; Kawata, M.; Tsuji, J.; Saito, S.; Moriwake, T. J. Org. Chem. 1990, 55, 5671-5673. (j) Suzuki, M.; Kayano, H.; Noyori, R.; Hashimoto, H.; Negishi, M.; Ichikawa, A.; Ito, S. Tetrahedron 1992, 48, 2635-2658. (k) Park, H.; Lee, Y. S.; Jung, S. H.; Shim, S. C. Synth. Commun. 1992, 22, 1445-1452. (l) Park, H.; Lee, Y. S.; Shim, S. C. Bull. Korean Chem. Soc. 1993, 14, 86-91. (m) Mikami, K.; Toshida, A. Synlett 1995, 29-31. (n) Mikami, K.; Yoshida, A.; Matsumoto, Y. Tetrahedron Lett. 1996, 37, 8515-8518. (o) Bund, J.; Gais, H.-J.; Schmitz, E.; Erdelmeier, I.; Raabe, G. Eur. J. Org. Chem. 1998, 1319-1335.
18. For the enantioselective synthesis of 1, see: (a) Shibasaki, M.; Fukasawa, H.; Ikegami, S. Tetrahedron Lett. 1983, 24, 3497-3500. (b) Torisawa, Y.; Okabe, H.; Shibasaki, M.; Ikegami, S. Chem. Lett. 1984, 1069-1072. (c) Sodeoka, M.; Shibasaki, M. Chem. Lett. 1984, 579-582. (d) Mase, T.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1984, 25, 5087-5090. (e) Torisawa, Y.; Okabe, H.; Ikegami, S. J. Chem. Soc., Chem. Commun. 1984, 1602-1603. (f) Ogawa, Y.; Shibasaki, M. Tetrahedron Lett. 1984, 25, 1067-1070. (g) Bannai, K.; Tanaka, T.; Okamura, N.; Hazato, A.; Sugiura, S.; Manabe, K.; Tomimori, T.; Kurozumi, S. Tetrahedron Lett. 1986, 27, 6353-6356. (h) Suzuki, M.; Koyano, H.; Noyori, R. J. Org. Chem. 1987, 52, 5583-5588. (i) Mandai, T.; Matsumoto, S.; Kohama, M.; Kawata, M.; Tsuji, J.; Saito, S.; Moriwake, T. J. Org. Chem. 1990, 55, 5671-5673. (j) Suzuki, M.; Kayano, H.; Noyori, R.; Hashimoto, H.; Negishi, M.; Ichikawa, A.; Ito, S. Tetrahedron 1992, 48, 2635-2658. (k) Park, H.; Lee, Y. S.; Jung, S. H.; Shim, S. C. Synth. Commun. 1992, 22, 1445-1452. (l) Park, H.; Lee, Y. S.; Shim, S. C. Bull. Korean Chem. Soc. 1993, 14, 86-91. (m) Mikami, K.; Toshida, A. Synlett 1995, 29-31. (n) Mikami, K.; Yoshida, A.; Matsumoto, Y. Tetrahedron Lett. 1996, 37, 8515-8518. (o) Bund, J.; Gais, H.-J.; Schmitz, E.; Erdelmeier, I.; Raabe, G. Eur. J. Org. Chem. 1998, 1319-1335.
19. For the enantioselective synthesis of 1, see: (a) Shibasaki, M.; Fukasawa, H.; Ikegami, S. Tetrahedron Lett. 1983, 24, 3497-3500. (b) Torisawa, Y.; Okabe, H.; Shibasaki, M.; Ikegami, S. Chem. Lett. 1984, 1069-1072. (c) Sodeoka, M.; Shibasaki, M. Chem. Lett. 1984, 579-582. (d) Mase, T.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1984, 25, 5087-5090. (e) Torisawa, Y.; Okabe, H.; Ikegami, S. J. Chem. Soc., Chem. Commun. 1984, 1602-1603. (f) Ogawa, Y.; Shibasaki, M. Tetrahedron Lett. 1984, 25, 1067-1070. (g) Bannai, K.; Tanaka, T.; Okamura, N.; Hazato, A.; Sugiura, S.; Manabe, K.; Tomimori, T.; Kurozumi, S. Tetrahedron Lett. 1986, 27, 6353-6356. (h) Suzuki, M.; Koyano, H.; Noyori, R. J. Org. Chem. 1987, 52, 5583-5588. (i) Mandai, T.; Matsumoto, S.; Kohama, M.; Kawata, M.; Tsuji, J.; Saito, S.; Moriwake, T. J. Org. Chem. 1990, 55, 5671-5673. (j) Suzuki, M.; Kayano, H.; Noyori, R.; Hashimoto, H.; Negishi, M.; Ichikawa, A.; Ito, S. Tetrahedron 1992, 48, 2635-2658. (k) Park, H.; Lee, Y. S.; Jung, S. H.; Shim, S. C. Synth. Commun. 1992, 22, 1445-1452. (l) Park, H.; Lee, Y. S.; Shim, S. C. Bull. Korean Chem. Soc. 1993, 14, 86-91. (m) Mikami, K.; Toshida, A. Synlett 1995, 29-31. (n) Mikami, K.; Yoshida, A.; Matsumoto, Y. Tetrahedron Lett. 1996, 37, 8515-8518. (o) Bund, J.; Gais, H.-J.; Schmitz, E.; Erdelmeier, I.; Raabe, G. Eur. J. Org. Chem. 1998, 1319-1335.
20. For the enantioselective synthesis of 1, see: (a) Shibasaki, M.; Fukasawa, H.; Ikegami, S. Tetrahedron Lett. 1983, 24, 3497-3500. (b) Torisawa, Y.; Okabe, H.; Shibasaki, M.; Ikegami, S. Chem. Lett. 1984, 1069-1072. (c) Sodeoka, M.; Shibasaki, M. Chem. Lett. 1984, 579-582. (d) Mase, T.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1984, 25, 5087-5090. (e) Torisawa, Y.; Okabe, H.; Ikegami, S. J. Chem. Soc., Chem. Commun. 1984, 1602-1603. (f) Ogawa, Y.; Shibasaki, M. Tetrahedron Lett. 1984, 25, 1067-1070. (g) Bannai, K.; Tanaka, T.; Okamura, N.; Hazato, A.; Sugiura, S.; Manabe, K.; Tomimori, T.; Kurozumi, S. Tetrahedron Lett. 1986, 27, 6353-6356. (h) Suzuki, M.; Koyano, H.; Noyori, R. J. Org. Chem. 1987, 52, 5583-5588. (i) Mandai, T.; Matsumoto, S.; Kohama, M.; Kawata, M.; Tsuji, J.; Saito, S.; Moriwake, T. J. Org. Chem. 1990, 55, 5671-5673. (j) Suzuki, M.; Kayano, H.; Noyori, R.; Hashimoto, H.; Negishi, M.; Ichikawa, A.; Ito, S. Tetrahedron 1992, 48, 2635-2658. (k) Park, H.; Lee, Y. S.; Jung, S. H.; Shim, S. C. Synth. Commun. 1992, 22, 1445-1452. (l) Park, H.; Lee, Y. S.; Shim, S. C. Bull. Korean Chem. Soc. 1993, 14, 86-91. (m) Mikami, K.; Toshida, A. Synlett 1995, 29-31. (n) Mikami, K.; Yoshida, A.; Matsumoto, Y. Tetrahedron Lett. 1996, 37, 8515-8518. (o) Bund, J.; Gais, H.-J.; Schmitz, E.; Erdelmeier, I.; Raabe, G. Eur. J. Org. Chem. 1998, 1319-1335.
21. For the enantioselective synthesis of 1, see: (a) Shibasaki, M.; Fukasawa, H.; Ikegami, S. Tetrahedron Lett. 1983, 24, 3497-3500. (b) Torisawa, Y.; Okabe, H.; Shibasaki, M.; Ikegami, S. Chem. Lett. 1984, 1069-1072. (c) Sodeoka, M.; Shibasaki, M. Chem. Lett. 1984, 579-582. (d) Mase, T.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1984, 25, 5087-5090. (e) Torisawa, Y.; Okabe, H.; Ikegami, S. J. Chem. Soc., Chem. Commun. 1984, 1602-1603. (f) Ogawa, Y.; Shibasaki, M. Tetrahedron Lett. 1984, 25, 1067-1070. (g) Bannai, K.; Tanaka, T.; Okamura, N.; Hazato, A.; Sugiura, S.; Manabe, K.; Tomimori, T.; Kurozumi, S. Tetrahedron Lett. 1986, 27, 6353-6356. (h) Suzuki, M.; Koyano, H.; Noyori, R. J. Org. Chem. 1987, 52, 5583-5588. (i) Mandai, T.; Matsumoto, S.; Kohama, M.; Kawata, M.; Tsuji, J.; Saito, S.; Moriwake, T. J. Org. Chem. 1990, 55, 5671-5673. (j) Suzuki, M.; Kayano, H.; Noyori, R.; Hashimoto, H.; Negishi, M.; Ichikawa, A.; Ito, S. Tetrahedron 1992, 48, 2635-2658. (k) Park, H.; Lee, Y. S.; Jung, S. H.; Shim, S. C. Synth. Commun. 1992, 22, 1445-1452. (l) Park, H.; Lee, Y. S.; Shim, S. C. Bull. Korean Chem. Soc. 1993, 14, 86-91. (m) Mikami, K.; Toshida, A. Synlett 1995, 29-31. (n) Mikami, K.; Yoshida, A.; Matsumoto, Y. Tetrahedron Lett. 1996, 37, 8515-8518. (o) Bund, J.; Gais, H.-J.; Schmitz, E.; Erdelmeier, I.; Raabe, G. Eur. J. Org. Chem. 1998, 1319-1335.
22. Ishikawa, T.; Shimizu, K.; Ishii, H.; Ikeda, S.; Saito, S. J. Org. Chem. 2001, 66, 3834-3847.
23. Wei, C. C.; Bernard, S. D.; Tengi, J. P.; Borgese, J.; Weigele, M. J. Org. Chem. 1985, 50, 3462-3467.
24. Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 36, 3769-3772.
25. 3CN (65°C, 11 h). The present larger-scale case resulted in a better yield (78%) during a shortened reaction time (3 h). Elucidation for the exact nature of this significant scale effect must await future systematic studies.
26. For the determination of relative configurations, see ref 7.
27. Belanger, D. B.; Livinghouse, T. Tetrahedron Lett. 1998, 39, 7641-7644.
28. No effort has been made to improve this ratio. Aldol reaction between 9 and (2E)-octenal led to a diastereomeric ratio of 1:2 in preference of the undesired β-isomer (10β) (LDA, THF, -78°C, 1 h, and then the aldehyde, -78°C, 50 min).
29. (a) Yamashita, M.; Tanaka, Y.; Arita, A.; Nishida, M. J. Org. Chem. 1994, 59, 3500-3502.
30. (b) Bargues, V.; Blay, G.; Cardona, L.; Garcia, B.; Pedro, J. R. Tetrahedron 1998, 54, 1845-1852.
31. For example, see: Saito, S.; Kuroda, A.; Matsunaga, H.; Ikeda, S. Tetrahedron 1996, 52, 13919-13932 and references therein.
32. For a review regarding the cleavage of cyclic ortho-esters, see: Block, E. Org. React. 1984, 30, 457-566.