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Enantioselective total synthesis of (+)-lithospermic acid.

ABSTRACT: An enantioselective synthesis of (+)-lithospermic acid, a potent anti-HIV agent, has been accomplished in a convergent manner in nine steps. The synthesis features an enantioselective intramolecular oxa-Michael addition catalyzed by a quinidine derivative, a hypervalent iodine-mediated rearrangement of chromanone to dihydrobenzofuran, an enantioselective ?-oxyamination, and an intermolecular C-H olefination.

SUBMITTER: Ghosh AK

PROVIDER: S-EPMC3482163 | biostudies-literature | 2012 Oct

REPOSITORIES: biostudies-literature

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Enantioselective total synthesis of (+)-lithospermic acid.

Ghosh Arun K AK Cheng Xu X Zhou Bing B

Organic letters 20120914 19

An enantioselective synthesis of (+)-lithospermic acid, a potent anti-HIV agent, has been accomplished in a convergent manner in nine steps. The synthesis features an enantioselective intramolecular oxa-Michael addition catalyzed by a quinidine derivative, a hypervalent iodine-mediated rearrangement of chromanone to dihydrobenzofuran, an enantioselective α-oxyamination, and an intermolecular C-H olefination. ...[more]

PMID: 22978790

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