205584-90-3

Upstream product

• 127661-25-0 (S)-benzyl 2-hydroxy-2-((S)-2-methyloxiran-2-yl)acetate 
• 879-18-5 naphthalene-1-carbonic acid chloride 
• 541-47-9 3-Methylbutenoic acid 
• 37526-89-9 benzyl 3-methylbut-2-enoate 
• 100-39-0 benzyl bromide 
• 157087-28-0 (S)-benzyl 2-hydroxy-3-methylbut-3-enoate 
• 205584-89-0 (S)-benzyl 3,3-dimethyloxirane-2-carboxylate 
• 184528-78-7 (R)-1-((benzyloxy)carbonyl)-2-hydroxy-2-methylpropyl methanesulfonate 
• 184528-76-5 (R)-benzyl 2,3-dihydroxy-3-methylbutanoate 

Relevant academic research and scientific papers

Delineating noncovalent interactions between the azinomycins and double-stranded DNA: Importance of the naphthalene substitution pattern on interstrand cross-linking efficiency

(Chemical Equation Presented) Using a series of synthetic azinomycin analogues, it is shown that the efficiency of in vitro DNA interstrand cross-linking is markedly reduced when either the C-5′ methyl group or both the C-5′ methyl and C-3′ methoxy groups

Chemical synthesis and cytotoxicity of some azinomycin analogues devoid of the 1-azabicyclo[3.1.0]hexane subunit

A series of compounds related to the left-hand domain of the azinomycins have been made and evaluated for cytotoxic activity against a small panel of human tumour cell lines. The epoxide ring is shown to be essential for biological activity. Cytotoxicity is also shown to be sensitive to changes in the substitution pattern on the aromatic ring and the amide group. (C) 2000 Elsevier Science Ltd. All rights reserved.

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-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.