Issue 7, 1998
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Asymmetric synthesis of the left hand portion of the azinomycins

Helen J. Bryant,   Christophe Y. Dardonville,   Timothy J. Hodgkinson,   Michael B. Hursthouse,   K. M. Abdul Malik  and  Michael Shipman  

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.

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DOI
https://doi.org/10.1039/A709084F
Article type
Paper

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

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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

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