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A protecting group-free synthesis of (-)-hortonones A-C from the Inhoffen-Lythgoe diol.

ABSTRACT: A synthesis of hortonones A-C has been accomplished from vitamin D2via the Inhoffen-Lythgoe diol without the use of protective groups. Key steps in the syntheses include a TMS-diazomethane mediated regioselective homologation of the cyclohexanone ring to a cycloheptanone moiety and a sodium naphthalenide-mediated allylic alcohol transposition. It has been found that the absolute configuration of the natural hortonones is opposite that of the synthetic material prepared from vitamin D2.

SUBMITTER: Stambulyan H

PROVIDER: S-EPMC5088714 | biostudies-literature | 2016 Sep

REPOSITORIES: biostudies-literature

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A protecting group-free synthesis of (-)-hortonones A-C from the Inhoffen-Lythgoe diol.

Stambulyan Hovsep H Minehan Thomas G TG

Organic & biomolecular chemistry 20160901 37

A synthesis of hortonones A-C has been accomplished from vitamin D<sub>2</sub>via the Inhoffen-Lythgoe diol without the use of protective groups. Key steps in the syntheses include a TMS-diazomethane mediated regioselective homologation of the cyclohexanone ring to a cycloheptanone moiety and a sodium naphthalenide-mediated allylic alcohol transposition. It has been found that the absolute configuration of the natural hortonones is opposite that of the synthetic material prepared from vitamin D< ...[more]

PMID: 27714252

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