How stable are epoxides? A novel synthesis of epothilone B

Angewandte Chemie - International Edition

Volumn 39, Issue 3, 2000, Pages 581-583

  Martin, Harry J ^a   Drescher, Martina ^a   Mulzer, Johann ^a  

^a INSTITUT FÜR ORGANISCHE CHEMIE   (Austria)

Author keywords

Aldol reactions; Dihydroxylations; Epoxidations; Olefinations; Total synthesis

Indexed keywords

ANTINEOPLASTIC AGENT; EPOTHILONE B; EPOXIDE;

ARTICLE; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0034603098     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(20000204)39:3<581::AID-ANIE581>3.0.CO;2-W     Document Type: Article

References (31)

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24. a) Review: J. Gorzynski Smith, Synthesis 1983, 629; epoxides as intermediates in natural product syntheses: b) Monensin: G. Schmid, T. Tukuyama, K. Akasaka, Y. Kishi, J. Am. Chem. Soc. 1979, 101, 259; c) Ionomycin A: D. A. Evans, A. M. Ratz, B. E. Huff, G. S. Sheppard, J. Am. Chem. Soc. 1995, 117, 3448; d) brevetoxin: K. C. Nicolaou, Angew. Chem. 1996, 108, 644; Angew. Chem. Int. Ed. Engl. 1996, 35, 589. Regarding the stability of "early" epoxides in total synthesis see: e) E. J. Corey, B. B. Snider, J. Am. Chem. Soc. 1972, 94, 2549; f) E. J. Corey, J. P. Dittami, J. Am. Chem. Soc. 1985, 107, 256; g) D. A. Evans, A. S. Kim, R. Metternich, V. J. Novack, J. Am. Chem. Soc. 1998, 120, 5921.
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