861997-79-7

Upstream product

• 861997-78-6 1-(1-phenyl-1H-tetrazole-5-sulfonyl)-heptadecan-8-one 
• 7381-30-8 2,2,7,7-tetramethyl-3,6-dioxa-2,7-disilaoctane 
• 777891-09-5 tert-butyl-(7-iodo-heptyloxy)-diphenyl-silane 
• 861997-73-1 7-(2-nonyl-[1,3]dithian-2-yl)-heptan-1-ol 
• 861997-77-5 1-(1-phenyl-1H-tetrazol-5-ylsulfanyl)-heptadecan-8-one 
• 861997-74-2 5-[7-(2-nonyl-[1,3]dithian-2-yl)-heptylsulfanyl]-1-phenyl-1H-tetrazole 
• 629-30-1 1,7-heptandiol 
• 42196-81-6 2-nonyl-1,3-dithiane 
• 693-58-3 1-Bromononane 
• 89940-48-7 7-iodo-1-heptanol 

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.