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Issue 37, 2016
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A protecting group-free synthesis of (−)-hortonones A–C from the Inhoffen–Lythgoe diol

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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.

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

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Publication details

The article was received on 11 Aug 2016, accepted on 22 Aug 2016 and first published on 22 Aug 2016


Article type: Paper
DOI: 10.1039/C6OB01738J
Citation: Org. Biomol. Chem., 2016,14, 8728-8731
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    A protecting group-free synthesis of (−)-hortonones A–C from the Inhoffen–Lythgoe diol

    H. Stambulyan and T. G. Minehan, Org. Biomol. Chem., 2016, 14, 8728
    DOI: 10.1039/C6OB01738J

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