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