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Volumn 43, Issue 47, 2004, Pages 6505-6510

A formal total synthesis of (+)-pinnatoxin A

Author keywords

Heterocycles; Macrocycles; Natural products; Spiro compounds; Total synthesis

Indexed keywords

AROMATIC COMPOUNDS; CARBON; SYNTHESIS (CHEMICAL);

EID: 11144270139     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200461802     Document Type: Article
Times cited : (65)

References (65)
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    • For the structural determination of related molecules, see: pinnatoxin B.C: a) N. Takada, N. Umemura, K. Suenaga, T. Chou, A. Nagatsu, T. Haino, K. Yamada, D. Uemura, Tetrahedron Lett. 2001, 42, 3491-3494; pinnatoxin D: b) T. Chou, T. Haino, M. Kuramoto, D. Uemura, Tetrahedron Lett. 1996, 37, 4027-4030; spirolides: c) T. Hu, J. M. Curtis, Y. Oshima, M. A. Quilliam, J. A. Walter, W. M. Watson-Wright, J. L. C. Wright, J. Chem. Soc. Chem. Commun. 1995, 2159-2161; d) M. Falk, I. W. Burton, T. Hu, J. A. Walter, J. L. C. Wright, Tetrahedron 2001, 57, 8659-8665; pteriatoxins: e) N. Takada, N. Umemura, K. Suenaga, D. Uemura, Tetrahedron Lett. 2001, 42, 3495-3497.
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    • For the structural determination of related molecules, see: pinnatoxin B.C: a) N. Takada, N. Umemura, K. Suenaga, T. Chou, A. Nagatsu, T. Haino, K. Yamada, D. Uemura, Tetrahedron Lett. 2001, 42, 3491-3494; pinnatoxin D: b) T. Chou, T. Haino, M. Kuramoto, D. Uemura, Tetrahedron Lett. 1996, 37, 4027-4030; spirolides: c) T. Hu, J. M. Curtis, Y. Oshima, M. A. Quilliam, J. A. Walter, W. M. Watson-Wright, J. L. C. Wright, J. Chem. Soc. Chem. Commun. 1995, 2159-2161; d) M. Falk, I. W. Burton, T. Hu, J. A. Walter, J. L. C. Wright, Tetrahedron 2001, 57, 8659-8665; pteriatoxins: e) N. Takada, N. Umemura, K. Suenaga, D. Uemura, Tetrahedron Lett. 2001, 42, 3495-3497.
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    • For the structural determination of related molecules, see: pinnatoxin B.C: a) N. Takada, N. Umemura, K. Suenaga, T. Chou, A. Nagatsu, T. Haino, K. Yamada, D. Uemura, Tetrahedron Lett. 2001, 42, 3491-3494; pinnatoxin D: b) T. Chou, T. Haino, M. Kuramoto, D. Uemura, Tetrahedron Lett. 1996, 37, 4027-4030; spirolides: c) T. Hu, J. M. Curtis, Y. Oshima, M. A. Quilliam, J. A. Walter, W. M. Watson-Wright, J. L. C. Wright, J. Chem. Soc. Chem. Commun. 1995, 2159-2161; d) M. Falk, I. W. Burton, T. Hu, J. A. Walter, J. L. C. Wright, Tetrahedron 2001, 57, 8659-8665; pteriatoxins: e) N. Takada, N. Umemura, K. Suenaga, D. Uemura, Tetrahedron Lett. 2001, 42, 3495-3497.
    • (2001) Tetrahedron , vol.57 , pp. 8659-8665
    • Falk, M.1    Burton, I.W.2    Hu, T.3    Walter, J.A.4    Wright, J.L.C.5
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    • 0035858695 scopus 로고    scopus 로고
    • For the structural determination of related molecules, see: pinnatoxin B.C: a) N. Takada, N. Umemura, K. Suenaga, T. Chou, A. Nagatsu, T. Haino, K. Yamada, D. Uemura, Tetrahedron Lett. 2001, 42, 3491-3494; pinnatoxin D: b) T. Chou, T. Haino, M. Kuramoto, D. Uemura, Tetrahedron Lett. 1996, 37, 4027-4030; spirolides: c) T. Hu, J. M. Curtis, Y. Oshima, M. A. Quilliam, J. A. Walter, W. M. Watson-Wright, J. L. C. Wright, J. Chem. Soc. Chem. Commun. 1995, 2159-2161; d) M. Falk, I. W. Burton, T. Hu, J. A. Walter, J. L. C. Wright, Tetrahedron 2001, 57, 8659-8665; pteriatoxins: e) N. Takada, N. Umemura, K. Suenaga, D. Uemura, Tetrahedron Lett. 2001, 42, 3495-3497.
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    • Takada, N.1    Umemura, N.2    Suenaga, K.3    Uemura, D.4
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    • For synthetic studies of 1 from this laboratory, see: a) T. Noda, A. Ishiwata, S. Uemura, S. Sakamoto, M. Hirama, Synlett 1998, 298-300; b) A. Ishiwata, S. Sakamoto, T. Noda, M. Hirama, Synlett 1999, 692-694; c) A. Nitta, A. Ishiwata, T. Noda, M. Hirama, Synlett 1999, 695-696; d) J. Wang, S. Sakamoto, K. Kamada, A. Nitta, T. Noda, H. Oguri, M. Hirama, Synlett 2003, 891-893.
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    • For synthetic studies of 1 from this laboratory, see: a) T. Noda, A. Ishiwata, S. Uemura, S. Sakamoto, M. Hirama, Synlett 1998, 298-300; b) A. Ishiwata, S. Sakamoto, T. Noda, M. Hirama, Synlett 1999, 692-694; c) A. Nitta, A. Ishiwata, T. Noda, M. Hirama, Synlett 1999, 695-696; d) J. Wang, S. Sakamoto, K. Kamada, A. Nitta, T. Noda, H. Oguri, M. Hirama, Synlett 2003, 891-893.
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    • Ishiwata, A.1    Sakamoto, S.2    Noda, T.3    Hirama, M.4
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    • For synthetic studies of 1 from this laboratory, see: a) T. Noda, A. Ishiwata, S. Uemura, S. Sakamoto, M. Hirama, Synlett 1998, 298-300; b) A. Ishiwata, S. Sakamoto, T. Noda, M. Hirama, Synlett 1999, 692-694; c) A. Nitta, A. Ishiwata, T. Noda, M. Hirama, Synlett 1999, 695-696; d) J. Wang, S. Sakamoto, K. Kamada, A. Nitta, T. Noda, H. Oguri, M. Hirama, Synlett 2003, 891-893.
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    • Nitta, A.1    Ishiwata, A.2    Noda, T.3    Hirama, M.4
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    • For synthetic studies of 1 from this laboratory, see: a) T. Noda, A. Ishiwata, S. Uemura, S. Sakamoto, M. Hirama, Synlett 1998, 298-300; b) A. Ishiwata, S. Sakamoto, T. Noda, M. Hirama, Synlett 1999, 692-694; c) A. Nitta, A. Ishiwata, T. Noda, M. Hirama, Synlett 1999, 695-696; d) J. Wang, S. Sakamoto, K. Kamada, A. Nitta, T. Noda, H. Oguri, M. Hirama, Synlett 2003, 891-893.
    • (2003) Synlett , pp. 891-893
    • Wang, J.1    Sakamoto, S.2    Kamada, K.3    Nitta, A.4    Noda, T.5    Oguri, H.6    Hirama, M.7
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    • 0030796269 scopus 로고    scopus 로고
    • For synthetic studies of 1 from other laboratories, see: a) T. Sugimoto, J. Ishihara, A. Murai, Tetrahedron Lett. 1997, 38, 7379-7382; b) J. Ishihara, T. Sugimoto, A. Murai, Synlett 1998, 603-606; c) B. D. Suthers, M. F. Jacobs, W. Kitching, Tetrahedron Lett. 1998, 39, 2621-2624; d) T. Sugimoto, J. Ishihara, A. Murai, Synlett 1999, 541-544; e) J. Ishihara, S. Tojo, A. Kamikawa, A. Murai, Chem. Commun. 2001, 1392-1393; f) S. Nakamura, J. Inagaki, T. Sugimoto, M. Kudo, M. Nakajima, S. Hashimoto, Org. Lett. 2001, 3, 4075-4078; g) S. Nakamura, J. Inagaki, M. Kudo, T. Sugimoto, K. Obara, M. Nakajima, S. Hashimoto, Tetrahedron 2002, 58, 10353-10374; h) S. Nakamura, J. Inagaki, T. Sugimoto, Y. Ura, S. Hashimoto, Tetrahedron 2002, 58, 10375-10386.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 7379-7382
    • Sugimoto, T.1    Ishihara, J.2    Murai, A.3
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    • For synthetic studies of 1 from other laboratories, see: a) T. Sugimoto, J. Ishihara, A. Murai, Tetrahedron Lett. 1997, 38, 7379-7382; b) J. Ishihara, T. Sugimoto, A. Murai, Synlett 1998, 603-606; c) B. D. Suthers, M. F. Jacobs, W. Kitching, Tetrahedron Lett. 1998, 39, 2621-2624; d) T. Sugimoto, J. Ishihara, A. Murai, Synlett 1999, 541-544; e) J. Ishihara, S. Tojo, A. Kamikawa, A. Murai, Chem. Commun. 2001, 1392-1393; f) S. Nakamura, J. Inagaki, T. Sugimoto, M. Kudo, M. Nakajima, S. Hashimoto, Org. Lett. 2001, 3, 4075-4078; g) S. Nakamura, J. Inagaki, M. Kudo, T. Sugimoto, K. Obara, M. Nakajima, S. Hashimoto, Tetrahedron 2002, 58, 10353-10374; h) S. Nakamura, J. Inagaki, T. Sugimoto, Y. Ura, S. Hashimoto, Tetrahedron 2002, 58, 10375-10386.
    • (1998) Synlett , pp. 603-606
    • Ishihara, J.1    Sugimoto, T.2    Murai, A.3
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    • 0032559951 scopus 로고    scopus 로고
    • For synthetic studies of 1 from other laboratories, see: a) T. Sugimoto, J. Ishihara, A. Murai, Tetrahedron Lett. 1997, 38, 7379-7382; b) J. Ishihara, T. Sugimoto, A. Murai, Synlett 1998, 603-606; c) B. D. Suthers, M. F. Jacobs, W. Kitching, Tetrahedron Lett. 1998, 39, 2621-2624; d) T. Sugimoto, J. Ishihara, A. Murai, Synlett 1999, 541-544; e) J. Ishihara, S. Tojo, A. Kamikawa, A. Murai, Chem. Commun. 2001, 1392-1393; f) S. Nakamura, J. Inagaki, T. Sugimoto, M. Kudo, M. Nakajima, S. Hashimoto, Org. Lett. 2001, 3, 4075-4078; g) S. Nakamura, J. Inagaki, M. Kudo, T. Sugimoto, K. Obara, M. Nakajima, S. Hashimoto, Tetrahedron 2002, 58, 10353-10374; h) S. Nakamura, J. Inagaki, T. Sugimoto, Y. Ura, S. Hashimoto, Tetrahedron 2002, 58, 10375-10386.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 2621-2624
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    • 0032939222 scopus 로고    scopus 로고
    • For synthetic studies of 1 from other laboratories, see: a) T. Sugimoto, J. Ishihara, A. Murai, Tetrahedron Lett. 1997, 38, 7379-7382; b) J. Ishihara, T. Sugimoto, A. Murai, Synlett 1998, 603-606; c) B. D. Suthers, M. F. Jacobs, W. Kitching, Tetrahedron Lett. 1998, 39, 2621-2624; d) T. Sugimoto, J. Ishihara, A. Murai, Synlett 1999, 541-544; e) J. Ishihara, S. Tojo, A. Kamikawa, A. Murai, Chem. Commun. 2001, 1392-1393; f) S. Nakamura, J. Inagaki, T. Sugimoto, M. Kudo, M. Nakajima, S. Hashimoto, Org. Lett. 2001, 3, 4075-4078; g) S. Nakamura, J. Inagaki, M. Kudo, T. Sugimoto, K. Obara, M. Nakajima, S. Hashimoto, Tetrahedron 2002, 58, 10353-10374; h) S. Nakamura, J. Inagaki, T. Sugimoto, Y. Ura, S. Hashimoto, Tetrahedron 2002, 58, 10375-10386.
    • (1999) Synlett , pp. 541-544
    • Sugimoto, T.1    Ishihara, J.2    Murai, A.3
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    • 0035822776 scopus 로고    scopus 로고
    • For synthetic studies of 1 from other laboratories, see: a) T. Sugimoto, J. Ishihara, A. Murai, Tetrahedron Lett. 1997, 38, 7379-7382; b) J. Ishihara, T. Sugimoto, A. Murai, Synlett 1998, 603-606; c) B. D. Suthers, M. F. Jacobs, W. Kitching, Tetrahedron Lett. 1998, 39, 2621-2624; d) T. Sugimoto, J. Ishihara, A. Murai, Synlett 1999, 541-544; e) J. Ishihara, S. Tojo, A. Kamikawa, A. Murai, Chem. Commun. 2001, 1392-1393; f) S. Nakamura, J. Inagaki, T. Sugimoto, M. Kudo, M. Nakajima, S. Hashimoto, Org. Lett. 2001, 3, 4075-4078; g) S. Nakamura, J. Inagaki, M. Kudo, T. Sugimoto, K. Obara, M. Nakajima, S. Hashimoto, Tetrahedron 2002, 58, 10353-10374; h) S. Nakamura, J. Inagaki, T. Sugimoto, Y. Ura, S. Hashimoto, Tetrahedron 2002, 58, 10375-10386.
    • (2001) Chem. Commun. , pp. 1392-1393
    • Ishihara, J.1    Tojo, S.2    Kamikawa, A.3    Murai, A.4
  • 18
    • 0035856898 scopus 로고    scopus 로고
    • For synthetic studies of 1 from other laboratories, see: a) T. Sugimoto, J. Ishihara, A. Murai, Tetrahedron Lett. 1997, 38, 7379-7382; b) J. Ishihara, T. Sugimoto, A. Murai, Synlett 1998, 603-606; c) B. D. Suthers, M. F. Jacobs, W. Kitching, Tetrahedron Lett. 1998, 39, 2621-2624; d) T. Sugimoto, J. Ishihara, A. Murai, Synlett 1999, 541-544; e) J. Ishihara, S. Tojo, A. Kamikawa, A. Murai, Chem. Commun. 2001, 1392-1393; f) S. Nakamura, J. Inagaki, T. Sugimoto, M. Kudo, M. Nakajima, S. Hashimoto, Org. Lett. 2001, 3, 4075-4078; g) S. Nakamura, J. Inagaki, M. Kudo, T. Sugimoto, K. Obara, M. Nakajima, S. Hashimoto, Tetrahedron 2002, 58, 10353-10374; h) S. Nakamura, J. Inagaki, T. Sugimoto, Y. Ura, S. Hashimoto, Tetrahedron 2002, 58, 10375-10386.
    • (2001) Org. Lett. , vol.3 , pp. 4075-4078
    • Nakamura, S.1    Inagaki, J.2    Sugimoto, T.3    Kudo, M.4    Nakajima, M.5    Hashimoto, S.6
  • 19
    • 0037164607 scopus 로고    scopus 로고
    • For synthetic studies of 1 from other laboratories, see: a) T. Sugimoto, J. Ishihara, A. Murai, Tetrahedron Lett. 1997, 38, 7379-7382; b) J. Ishihara, T. Sugimoto, A. Murai, Synlett 1998, 603-606; c) B. D. Suthers, M. F. Jacobs, W. Kitching, Tetrahedron Lett. 1998, 39, 2621-2624; d) T. Sugimoto, J. Ishihara, A. Murai, Synlett 1999, 541-544; e) J. Ishihara, S. Tojo, A. Kamikawa, A. Murai, Chem. Commun. 2001, 1392-1393; f) S. Nakamura, J. Inagaki, T. Sugimoto, M. Kudo, M. Nakajima, S. Hashimoto, Org. Lett. 2001, 3, 4075-4078; g) S. Nakamura, J. Inagaki, M. Kudo, T. Sugimoto, K. Obara, M. Nakajima, S. Hashimoto, Tetrahedron 2002, 58, 10353-10374; h) S. Nakamura, J. Inagaki, T. Sugimoto, Y. Ura, S. Hashimoto, Tetrahedron 2002, 58, 10375-10386.
    • (2002) Tetrahedron , vol.58 , pp. 10353-10374
    • Nakamura, S.1    Inagaki, J.2    Kudo, M.3    Sugimoto, T.4    Obara, K.5    Nakajima, M.6    Hashimoto, S.7
  • 20
    • 0037164673 scopus 로고    scopus 로고
    • For synthetic studies of 1 from other laboratories, see: a) T. Sugimoto, J. Ishihara, A. Murai, Tetrahedron Lett. 1997, 38, 7379-7382; b) J. Ishihara, T. Sugimoto, A. Murai, Synlett 1998, 603-606; c) B. D. Suthers, M. F. Jacobs, W. Kitching, Tetrahedron Lett. 1998, 39, 2621-2624; d) T. Sugimoto, J. Ishihara, A. Murai, Synlett 1999, 541-544; e) J. Ishihara, S. Tojo, A. Kamikawa, A. Murai, Chem. Commun. 2001, 1392-1393; f) S. Nakamura, J. Inagaki, T. Sugimoto, M. Kudo, M. Nakajima, S. Hashimoto, Org. Lett. 2001, 3, 4075-4078; g) S. Nakamura, J. Inagaki, M. Kudo, T. Sugimoto, K. Obara, M. Nakajima, S. Hashimoto, Tetrahedron 2002, 58, 10353-10374; h) S. Nakamura, J. Inagaki, T. Sugimoto, Y. Ura, S. Hashimoto, Tetrahedron 2002, 58, 10375-10386.
    • (2002) Tetrahedron , vol.58 , pp. 10375-10386
    • Nakamura, S.1    Inagaki, J.2    Sugimoto, T.3    Ura, Y.4    Hashimoto, S.5
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    • For synthetic studies of spirolides, see: a) D. P. Furkert, M. A. Brimble, Org. Lett. 2002, 4, 3655-3658; b) M. Trzoss, M. A. Brimble, Synlett 2003, 2042-2046, and references therein.
    • (2002) Org. Lett. , vol.4 , pp. 3655-3658
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    • and references therein
    • For synthetic studies of spirolides, see: a) D. P. Furkert, M. A. Brimble, Org. Lett. 2002, 4, 3655-3658; b) M. Trzoss, M. A. Brimble, Synlett 2003, 2042-2046, and references therein.
    • (2003) Synlett , pp. 2042-2046
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    • For reviews, see: a) A. Fürstner, Angew. Chem. 2000, 112, 3140-3172; Angew. Chem. Int. Ed. 2000, 39, 3013-3043; b) T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18-29; c) Handbook of Metathesis, Vol. 2 (Ed.: R. H. Grubbs), Wiley-VCH, Weinheim, 2003.
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    • For reviews, see: a) A. Fürstner, Angew. Chem. 2000, 112, 3140-3172; Angew. Chem. Int. Ed. 2000, 39, 3013-3043; b) T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18-29; c) Handbook of Metathesis, Vol. 2 (Ed.: R. H. Grubbs), Wiley-VCH, Weinheim, 2003.
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 3013-3043
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    • For reviews, see: a) A. Fürstner, Angew. Chem. 2000, 112, 3140-3172; Angew. Chem. Int. Ed. 2000, 39, 3013-3043; b) T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18-29; c) Handbook of Metathesis, Vol. 2 (Ed.: R. H. Grubbs), Wiley-VCH, Weinheim, 2003.
    • (2001) Acc. Chem. Res. , vol.34 , pp. 18-29
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    • Wiley-VCH, Weinheim
    • For reviews, see: a) A. Fürstner, Angew. Chem. 2000, 112, 3140-3172; Angew. Chem. Int. Ed. 2000, 39, 3013-3043; b) T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18-29; c) Handbook of Metathesis, Vol. 2 (Ed.: R. H. Grubbs), Wiley-VCH, Weinheim, 2003.
    • (2003) Handbook of Metathesis , vol.2
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    • For a recent review on synthesis of bis-spiroacetals, see: M. A. Brimble, F. F. Farès, Tetrahedron 1999, 55, 7661-7706.
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    • note
    • [4a] Furthermore, acidic treatment of a 10-OH-protected substrate resulted in nonselective formation of the desired spiroacetal and its C19-epimer despite the seemingly favorable anomeric effect at C19 of the desired compound.
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    • 2.
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    • note
    • The stereochemistry of C5 and C31 were determined by X-ray crystallographic analysis of an analogue derivatized from 29; see Supporting Information for detail.
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    • note
    • While initial treatment with TFA mainly removed the TMS and TES groups, the TIPS and acetonide groups were deprotected by subjection to CSA/MeOH. This stepwise deprotection scheme appears to be superior to a single-step approach in terms of yield.
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    • For related examples, see: a) B. M. Trost, S. R. Pulley, Tetrahedron Lett. 1995, 36, 8737-8740; b) J. Zhu, D. Ma, Angew. Chem. 2003, 115, 5506-5509; Angew. Chem. Int. Ed. 2003, 42, 5348-5351.
    • (2003) Angew. Chem. , vol.115 , pp. 5506-5509
    • Zhu, J.1    Ma, D.2
  • 64
    • 0344875940 scopus 로고    scopus 로고
    • For related examples, see: a) B. M. Trost, S. R. Pulley, Tetrahedron Lett. 1995, 36, 8737-8740; b) J. Zhu, D. Ma, Angew. Chem. 2003, 115, 5506-5509; Angew. Chem. Int. Ed. 2003, 42, 5348-5351.
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 5348-5351
  • 65
    • 11144264754 scopus 로고    scopus 로고
    • note
    • [7]


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.