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Stereocontrolled Synthesis of Kalihinol C.

ABSTRACT: We report a concise chemical synthesis of kalihinol C via a possible biosynthetic intermediate, "protokalihinol", which was targeted as a scaffold en route to antiplasmodial analogs. High stereocontrol of the kalihinol framework relies on a heterodendralene cascade to establish the target stereotetrad. Common problems of regio- and chemoselectivity encountered in the kalihinol class are explained and solved.

SUBMITTER: Reiher CA

PROVIDER: S-EPMC5854479 | biostudies-literature | 2017 Mar

REPOSITORIES: biostudies-literature

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Stereocontrolled Synthesis of Kalihinol C.

Reiher Christopher A CA Shenvi Ryan A RA

Journal of the American Chemical Society 20170302 10

We report a concise chemical synthesis of kalihinol C via a possible biosynthetic intermediate, "protokalihinol", which was targeted as a scaffold en route to antiplasmodial analogs. High stereocontrol of the kalihinol framework relies on a heterodendralene cascade to establish the target stereotetrad. Common problems of regio- and chemoselectivity encountered in the kalihinol class are explained and solved. ...[more]

PMID: 28252949

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