184758-45-0Relevant academic research and scientific papers
Synthesis of functional "top-half" partial structures of azinomycin A and B
Coleman, Robert S.,Tierney, Mark T.,Cortright, Sarah B.,Carper, Daniel J.
, p. 7726 - 7735 (2008/02/12)
(Chemical Equation Presented) The design and synthesis of a detailed series of functional "top-half substructures of azinomycin A and B is described.
Asymmetric synthesis of the left hand portion of the azinomycins
Bryant, Helen J.,Dardonville, Christophe Y.,Hodgkinson, Timothy J.,Hursthouse, Michael B.,Malik, K. M. Abdul,Shipman, Michael
, p. 1249 - 1255 (2007/10/03)
A nine step synthesis of the left hand portion of the azinomycins is described starting from 3,3-dimethyl-acrylic 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.
