Asymmetric synthesis of the left hand portion of the azinomycins

A nine step synthesis of the left hand portion of the azinomycins is described starting from 3,3-dimethylacrylic acid. The approach relies on a Sharpless asymmetric dihydroxylation (AD) reaction to install the requisite (2S,3S)-stereochemistry of epoxy alcohol 4. This epoxide is converted to crystal...

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Bibliographic Details
Published inJournal of the Chemical Society, Perkin Transactions 1 no. 7; pp. 1249 - 1255
Main Authors Bryant, HJ, Dardonville, CY, Hodgkinson, TJ, Hursthouse, MB, Malik, KMA, Shipman, M
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 07.04.1998
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CONVENIENT SYNTHESIS
ANTITUMOR ANTIBIOTICS
SEGMENT
STEREOCHEMISTRY
DEHYDROAMINO ACIDS
CARZINOPHILIN-A
FRAGMENT
CYTOTOXICITY
STEREOSELECTIVE SYNTHESIS
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Summary:A nine step synthesis of the left hand portion of the azinomycins is described starting from 3,3-dimethylacrylic acid. The approach relies on a Sharpless asymmetric dihydroxylation (AD) reaction to install the requisite (2S,3S)-stereochemistry of epoxy alcohol 4. This epoxide is converted to crystalline amide derivative 12 whose structure and absolute stereochemistry have been unambiguously established using X-ray crystallography, Coupling of epoxy alcohol (2S,3S)-4 with naphthoyl chloride 16 and subsequent manipulations furnish epoxy amide (2S,3S)-1 identical in all respects with the natural material.
ISSN:0300-922X
1364-5463
DOI:10.1039/a709084f