777891-01-7

Upstream product

• 100-39-0 benzyl bromide 
• 81028-03-7 (Z)-4-benzyloxy-but-2-en-1-ol 
• 60656-87-3 benzyloxyacetoaldehyde 
• 68972-96-3 (Z)-1,4-dibenzyloxy-2-butene 
• 861997-59-3 4-Benzyloxy-2-((Z)-4-benzyloxy-but-2-enyloxy)-3-hydroxy-butyric acid isopropyl ester 
• 861997-58-2 ((Z)-4-Benzyloxy-but-2-enyloxy)-acetic acid isopropyl ester 
• 861997-65-1 (Z)-(4-benzyloxybut-2-enyloxy)acetic acid 

Relevant academic research and scientific papers

Ester dienolate [2,3]-Wittig rearrangement in natural product synthesis: Diastereoselective total synthesis of the triester of viridiofungin A, A 2, and A4

An ester dienolate [2,3]-Wittig rearrangement was utilized to access the alkylated citric acid skeleton 6 that is characteristic for the viridiofungins and other members of the alkyl citrate family of secondary natural products. The [2,3]-sigmatropic rearrangement of (Z,Z)-15 provided the rearrangement product (±)-syn-16 in moderate yield and with very good diastereoselectivity. A Julia-Kocienski olefination efficiently served to connect the polar head (±)-syn-26 with the lipophilic tail (32a-c) of the viridiofungins. Amide formation between the racemic viridiofungin precursors 35a-c and the enantiomerically pure amino acid L-tyrosine methyl ester followed by preparative reversed-phase HPLC provided the isopropyl dimethyl ester of viridiofungin A ((+)-39a), A2 ((+)-39b), and A4 ((+)-39c) as well as the nonnatural diastereomers (-)-38a-c.