Application of the β-azidonation reaction to the synthesis of the antitumor alkaloid (+)-pancratistatin

Tetrahedron

Volumn 54, Issue 51, 1998, Pages 15509-15524

  Magnus, Philip ^a   Sebhat, Iyassu K ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

Alkaloid; Antitumor; Desymmetrization; Pancratistatin; Prochiral; Triisopropylsilyl (TIPS) enol ethers; azidonation

Indexed keywords

ANTINEOPLASTIC ALKALOID; PANCRATISTATIN; UNCLASSIFIED DRUG;

ARTICLE; DIASTEREOISOMER; DRUG SYNTHESIS; EPOXIDATION; HYDROGENATION; HYDROLYSIS; PRIORITY JOURNAL; REACTION ANALYSIS; REDUCTION;

EID: 0032542156     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00975-2     Document Type: Article

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32. 1H NMR. (equation presented)
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36. (24) The mechanism for the formation of 33 involves initial epoxide 32a, which can reversibly open to give 32b. Interception of 32b by m-chlorobenzoate leads to 32c, which through the ortho ester 32d can transfer the benzoate resulting in 32f. Proton loss from 32f gives 33. (equation presented)
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