37505-01-4Relevant articles and documents
Total synthesis and absolute configuration of avenolide, extracellular factor in Streptomyces avermitilis
Uchida, Miho,Takamatsu, Satoshi,Arima, Shiho,Miyamoto, Kiyoko T,Kitani, Shigeru,Nihira, Takuya,Ikeda, Haruo,Nagamitsu, Tohru
experimental part, p. 781 - 787 (2012/06/16)
The first total synthesis of extracellular factor, Avenolide, in Streptomyces avermitilis has been achieved using a convergent approach. The stereogenic centers in two key segments were installed using Sharpless epoxidation and dihydroxylation. This synthetic study allowed the determination of the absolute configuration of avenolide as 4S,10R, and yielded important information on its structure-activity relationship.
The absolute configuration and total synthesis of korormicin
Uehara, Hisatoshi,Oishi, Tohru,Yoshikawa, Kazuhiro,Mochida, Kenichi,Hirama, Masahiro
, p. 8641 - 8645 (2007/10/03)
The marine antibiotic korormicin, isolated from the culture filtrate of marine bacterial strain Pseudoalteromonas sp. F-420, specifically inhibits the growth of marine Gram-negative bacteria without affecting terrestrial species. The absolute configuration of korormicin was determined by the combination of a CD exciton chirality method and chemical degradation. Convergent total synthesis of korormicin has been also achieved.
Preparation of (2R,3S)-(-)- and (2S,3R)-(+)-2,3-Epoxy-2-methylbutanoic Acids and Some of Their Esters
Torres-Valencia, J. Martin,Cerda-Garcia-Rojas, Carlos M.,Joseph-Nathan, Pedro
, p. 1611 - 1616 (2007/10/02)
Enantiomerically pure (2R,3S)-(-)- and (2S,3R)-(+)-2,3-epoxy-2-methylbutanoic acids 7 and 8 were prepared from 2-methyl-2-butenoic acid 1 (tiglic acid).They were characterized by spectroscopic and optical activity data and their absolute configuration was determined by chemical correlation with (R)-(+)- and (S)-(-)-2-methyl-1,2-butanediols.The corresponding methyl (16 and 17), menthyl (3 and 4), and 9α-angeloyloxy-1-oxolongipin-2-en-7β-yl (14 and 15) esters were also prepared.