Enantioselective total synthesis of aspidophytine [13]

Journal of the American Chemical Society

Volumn 121, Issue 28, 1999, Pages 6771-6772

  He, Feng ^a   Bo, Yunxin ^a   Altom, Jason D ^a   Corey, E J ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ASPIDOPHYTINE; ASPIDOSPERMINE; INSECTICIDE; PHYTIC ACID CALCIUM MAGNESIUM SALT; UNCLASSIFIED DRUG;

CHEMICAL STRUCTURE; ISOLATION PROCEDURE; LETTER; PHYTOCHEMISTRY; REACTION ANALYSIS; SYNTHESIS;

EID: 0033591940     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9915201     Document Type: Letter

References (31)

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12. (a) For a recent review of aspidospermine alkaloid synthesis, see: Saxton, J. E. In The Alkaloids; Cordele, G. A.; Ed. Academic Press: New York, 1998; p 343. For pioneering earlier studies, see the following references. (b) Stork, G.; Dolfini, J. J. Am. Chem. Soc. 1963, 85, 2872. (c) Harley-Mason, J.; Kaplan, M. J. Chem. Soc., Chem. Commun. 1967, 915. (d) Büchi, G.; Matsumoto, K. E.; Nishimura, H. J. Am. Chem. Soc. 1971, 93, 3299. (e) Kuehne, M. E.; Roland, D. M.; Hafter, R. J. Org. Chem. 1978, 43, 3705. (f) Andriamialisoa, R. Z.; Langlois, N.; Langlois, J. J. Org. Chem. 1985, 50, 961. (g) Cardwell, K.; Hewitt, B.; Ladlow, M.; Magnus, P. J. Am. Chem. Soc. 1988, 110, 2242. (h) Overman, L. E.; Robertson, G. M. Robichaud, A. J. J. Am. Chem. Soc. 1991, 113, 2598.
13. (a) For a recent review of aspidospermine alkaloid synthesis, see: Saxton, J. E. In The Alkaloids; Cordele, G. A.; Ed. Academic Press: New York, 1998; p 343. For pioneering earlier studies, see the following references. (b) Stork, G.; Dolfini, J. J. Am. Chem. Soc. 1963, 85, 2872. (c) Harley-Mason, J.; Kaplan, M. J. Chem. Soc., Chem. Commun. 1967, 915. (d) Büchi, G.; Matsumoto, K. E.; Nishimura, H. J. Am. Chem. Soc. 1971, 93, 3299. (e) Kuehne, M. E.; Roland, D. M.; Hafter, R. J. Org. Chem. 1978, 43, 3705. (f) Andriamialisoa, R. Z.; Langlois, N.; Langlois, J. J. Org. Chem. 1985, 50, 961. (g) Cardwell, K.; Hewitt, B.; Ladlow, M.; Magnus, P. J. Am. Chem. Soc. 1988, 110, 2242. (h) Overman, L. E.; Robertson, G. M. Robichaud, A. J. J. Am. Chem. Soc. 1991, 113, 2598.
14. (a) For a recent review of aspidospermine alkaloid synthesis, see: Saxton, J. E. In The Alkaloids; Cordele, G. A.; Ed. Academic Press: New York, 1998; p 343. For pioneering earlier studies, see the following references. (b) Stork, G.; Dolfini, J. J. Am. Chem. Soc. 1963, 85, 2872. (c) Harley-Mason, J.; Kaplan, M. J. Chem. Soc., Chem. Commun. 1967, 915. (d) Büchi, G.; Matsumoto, K. E.; Nishimura, H. J. Am. Chem. Soc. 1971, 93, 3299. (e) Kuehne, M. E.; Roland, D. M.; Hafter, R. J. Org. Chem. 1978, 43, 3705. (f) Andriamialisoa, R. Z.; Langlois, N.; Langlois, J. J. Org. Chem. 1985, 50, 961. (g) Cardwell, K.; Hewitt, B.; Ladlow, M.; Magnus, P. J. Am. Chem. Soc. 1988, 110, 2242. (h) Overman, L. E.; Robertson, G. M. Robichaud, A. J. J. Am. Chem. Soc. 1991, 113, 2598.
15. (a) For a recent review of aspidospermine alkaloid synthesis, see: Saxton, J. E. In The Alkaloids; Cordele, G. A.; Ed. Academic Press: New York, 1998; p 343. For pioneering earlier studies, see the following references. (b) Stork, G.; Dolfini, J. J. Am. Chem. Soc. 1963, 85, 2872. (c) Harley-Mason, J.; Kaplan, M. J. Chem. Soc., Chem. Commun. 1967, 915. (d) Büchi, G.; Matsumoto, K. E.; Nishimura, H. J. Am. Chem. Soc. 1971, 93, 3299. (e) Kuehne, M. E.; Roland, D. M.; Hafter, R. J. Org. Chem. 1978, 43, 3705. (f) Andriamialisoa, R. Z.; Langlois, N.; Langlois, J. J. Org. Chem. 1985, 50, 961. (g) Cardwell, K.; Hewitt, B.; Ladlow, M.; Magnus, P. J. Am. Chem. Soc. 1988, 110, 2242. (h) Overman, L. E.; Robertson, G. M. Robichaud, A. J. J. Am. Chem. Soc. 1991, 113, 2598.
16. (a) For a recent review of aspidospermine alkaloid synthesis, see: Saxton, J. E. In The Alkaloids; Cordele, G. A.; Ed. Academic Press: New York, 1998; p 343. For pioneering earlier studies, see the following references. (b) Stork, G.; Dolfini, J. J. Am. Chem. Soc. 1963, 85, 2872. (c) Harley-Mason, J.; Kaplan, M. J. Chem. Soc., Chem. Commun. 1967, 915. (d) Büchi, G.; Matsumoto, K. E.; Nishimura, H. J. Am. Chem. Soc. 1971, 93, 3299. (e) Kuehne, M. E.; Roland, D. M.; Hafter, R. J. Org. Chem. 1978, 43, 3705. (f) Andriamialisoa, R. Z.; Langlois, N.; Langlois, J. J. Org. Chem. 1985, 50, 961. (g) Cardwell, K.; Hewitt, B.; Ladlow, M.; Magnus, P. J. Am. Chem. Soc. 1988, 110, 2242. (h) Overman, L. E.; Robertson, G. M. Robichaud, A. J. J. Am. Chem. Soc. 1991, 113, 2598.
17. (a) For a recent review of aspidospermine alkaloid synthesis, see: Saxton, J. E. In The Alkaloids; Cordele, G. A.; Ed. Academic Press: New York, 1998; p 343. For pioneering earlier studies, see the following references. (b) Stork, G.; Dolfini, J. J. Am. Chem. Soc. 1963, 85, 2872. (c) Harley-Mason, J.; Kaplan, M. J. Chem. Soc., Chem. Commun. 1967, 915. (d) Büchi, G.; Matsumoto, K. E.; Nishimura, H. J. Am. Chem. Soc. 1971, 93, 3299. (e) Kuehne, M. E.; Roland, D. M.; Hafter, R. J. Org. Chem. 1978, 43, 3705. (f) Andriamialisoa, R. Z.; Langlois, N.; Langlois, J. J. Org. Chem. 1985, 50, 961. (g) Cardwell, K.; Hewitt, B.; Ladlow, M.; Magnus, P. J. Am. Chem. Soc. 1988, 110, 2242. (h) Overman, L. E.; Robertson, G. M. Robichaud, A. J. J. Am. Chem. Soc. 1991, 113, 2598.
18. (a) For a recent review of aspidospermine alkaloid synthesis, see: Saxton, J. E. In The Alkaloids; Cordele, G. A.; Ed. Academic Press: New York, 1998; p 343. For pioneering earlier studies, see the following references. (b) Stork, G.; Dolfini, J. J. Am. Chem. Soc. 1963, 85, 2872. (c) Harley-Mason, J.; Kaplan, M. J. Chem. Soc., Chem. Commun. 1967, 915. (d) Büchi, G.; Matsumoto, K. E.; Nishimura, H. J. Am. Chem. Soc. 1971, 93, 3299. (e) Kuehne, M. E.; Roland, D. M.; Hafter, R. J. Org. Chem. 1978, 43, 3705. (f) Andriamialisoa, R. Z.; Langlois, N.; Langlois, J. J. Org. Chem. 1985, 50, 961. (g) Cardwell, K.; Hewitt, B.; Ladlow, M.; Magnus, P. J. Am. Chem. Soc. 1988, 110, 2242. (h) Overman, L. E.; Robertson, G. M. Robichaud, A. J. J. Am. Chem. Soc. 1991, 113, 2598.
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30. 16 to result in an specially potent dihydroxylation catalyst.
31. 4 procedure involving proteolytic cleavage with aqueous hydrochloric acid at reflux.