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A Concise Total Synthesis of (+)-Waihoensene Guided by Quaternary Center Analysis.

ABSTRACT: The four contiguous all-carbon quaternary centers of waihoensene, coupled with the absence of any traditional reactive functional groups other than a single alkene, render it a particularly challenging synthetic target among angular triquinane natural products. Here, we show that its polycyclic frame can be assembled concisely by using a strategically chosen quaternary center to guide the formation of the other three through judiciously selected C-C bond formation reactions. Those events, which included a unique Conia-ene cyclization and a challenging Pauson-Khand reaction, afforded a 17-step synthesis of the molecule in enantioenriched form.

SUBMITTER: Peng C

PROVIDER: S-EPMC7906115 | biostudies-literature | 2020 Aug

REPOSITORIES: biostudies-literature

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A Concise Total Synthesis of (+)-Waihoensene Guided by Quaternary Center Analysis.

Peng Cheng C Arya Piyush P Zhou Zhiyao Z Snyder Scott A SA

Angewandte Chemie (International ed. in English) 20200603 32

The four contiguous all-carbon quaternary centers of waihoensene, coupled with the absence of any traditional reactive functional groups other than a single alkene, render it a particularly challenging synthetic target among angular triquinane natural products. Here, we show that its polycyclic frame can be assembled concisely by using a strategically chosen quaternary center to guide the formation of the other three through judiciously selected C-C bond formation reactions. Those events, which ...[more]

PMID: 32330370

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