Asymmetric synthesis of the left hand portion of the azinomycins

HJ Bryant, CY Dardonville, TJ Hodgkinson…

Index: Bryant, Helen J.; Dardonville, Christophe Y.; Hodgkinson, Timothy J.; Hursthouse, Michael B.; Malik, K. M. Abdul; Shipman, Michael Journal of the Chemical Society - Perkin Transactions 1, 1998 , # 7 p. 1249 - 1255

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Citation Number: 25

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 (2, 3 [])-stereochemistry of epoxy alcohol 4. This epoxide is converted to crystalline amide deriva