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Asymmetric Total Synthesis of Ieodomycin B.

ABSTRACT: Ieodomycin B, which shows in vitro antimicrobial activity, was isolated from a marine Bacillus species. A novel asymmetric total synthetic approach to ieodomycin B using commercially available geraniol was achieved. The approach involves the generation of 1,3-trans-dihydroxyl at C-3 and C-5 positions via a Crimmins-modified Evans aldol reaction and a chelation-controlled Mukaiyama aldol reaction of a p-methoxybenzyl-protected aldehyde, as well as the generation of a lactone ring in a deprotection-lactonization one-pot reaction.

SUBMITTER: Lin S

PROVIDER: S-EPMC5295237 | biostudies-literature | 2017 Jan

REPOSITORIES: biostudies-literature

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Asymmetric Total Synthesis of Ieodomycin B.

Lin Shuangjie S Zhang Jianting J Zhang Zhibin Z Xu Tianxiang T Huang Shuangping S Wang Xiaoji X

Marine drugs 20170118 1

Ieodomycin B, which shows in vitro antimicrobial activity, was isolated from a marine Bacillus species. A novel asymmetric total synthetic approach to ieodomycin B using commercially available geraniol was achieved. The approach involves the generation of 1,3-trans-dihydroxyl at C-3 and C-5 positions via a Crimmins-modified Evans aldol reaction and a chelation-controlled Mukaiyama aldol reaction of a p-methoxybenzyl-protected aldehyde, as well as the generation of a lactone ...[more]

PMID: 28106760

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