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

A synthesis of hortonones A-C has been accomplished from vitamin D 2 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 naphth...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2016-09, Vol.14 (37), p.8728-8731
Main Authors: Stambulyan, Hovsep, Minehan, Thomas G
Format: Article
Language:English
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Summary:A synthesis of hortonones A-C has been accomplished from vitamin D 2 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 2 . Synthesis of (−)-hortonones A-C from vitamin D 2 reveals that the natural products are of opposite absolute configuration to originally proposed.
ISSN:1477-0520
1477-0539
DOI:10.1039/c6ob01738j