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Biomimetic Synthesis of Meroterpenoids by Dearomatization-Driven Polycyclization.

ABSTRACT: A biomimetic route to farnesyl pyrophosphate and dimethyl orsellinic acid (DMOA)-derived meroterpenoid scaffolds has yet to be reported despite great interest from the chemistry and biomedical research communities. A concise synthetic route with the potential to access DMOA-derived meroterpenoids is highly desirable to create a library of related compounds. Herein, we report novel dearomatization methodology followed by polyene cyclization to access DMOA-derived meroterpenoid frameworks in six steps from commercially available starting materials. Furthermore, several farnesyl alkene substrates were used to generate structurally novel, DMOA-derived meroterpenoid derivatives. DFT calculations combined with experimentation provided a rationale for the observed thermodynamic distribution of polycyclization products.

SUBMITTER: Powers Z

PROVIDER: S-EPMC6814491 | biostudies-literature | 2019 Nov

REPOSITORIES: biostudies-literature

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Biomimetic Synthesis of Meroterpenoids by Dearomatization-Driven Polycyclization.

Powers Zachary Z Scharf Adam A Cheng Andrea A Yang Feng F Himmelbauer Martin M Mitsuhashi Takaaki T Barra Lena L Taniguchi Yoshimasa Y Kikuchi Takashi T Fujita Makoto M Abe Ikuro I Porco John A JA

Angewandte Chemie (International ed. in English) 20190925 45

A biomimetic route to farnesyl pyrophosphate and dimethyl orsellinic acid (DMOA)-derived meroterpenoid scaffolds has yet to be reported despite great interest from the chemistry and biomedical research communities. A concise synthetic route with the potential to access DMOA-derived meroterpenoids is highly desirable to create a library of related compounds. Herein, we report novel dearomatization methodology followed by polyene cyclization to access DMOA-derived meroterpenoid frameworks in six s ...[more]

PMID: 31515901

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