Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.


Issue 7, 1998
Previous Article Next Article

Asymmetric synthesis of the left hand portion of the azinomycins

Abstract

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.

Back to tab navigation

Additions and corrections

Article information


J. Chem. Soc., Perkin Trans. 1, 1998, 1249-1256
Article type
Paper

Asymmetric synthesis of the left hand portion of the azinomycins

H. J. Bryant, C. Y. Dardonville, T. J. Hodgkinson, M. B. Hursthouse, K. M. Abdul Malik and M. Shipman, J. Chem. Soc., Perkin Trans. 1, 1998, 1249
DOI: 10.1039/A709084F

Search articles by author

Spotlight

Advertisements