Total synthesis of 10-isocyano-4-cadinene and determination of its absolute configuration

Organic Letters
Keisuke NishikawaFuyuhiko Matsuda

Abstract

The first enantioselective total synthesis of 10-isocyano-4-cadinene, a marine sesquiterpene isolated from nudibranchs of the family Phyllidiidae, was achieved. The cadinene is expected to be a novel nontoxic antifouling agent. In the synthesis, an intermolecular Diels-Alder reaction and a SmI(2)-induced Barbier-type reaction were employed as key steps. The absolute configuration of 10-isocyano-4-cadinene was determined to be (1S, 6S, 7R, 10S) on the basis of the total synthesis. Antifouling activities against Balanus amphitrite with both enantiomers of 10-isocyano-4-cadinene were also evaluated.

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Citations

Nov 21, 2012·Journal of Natural Products·Keisuke NishikawaFuyuhiko Matsuda
Apr 2, 2014·Journal of Chemical Ecology·Hsiao-Yung HoJocelyn G Millar
Jan 12, 2017·Organic & Biomolecular Chemistry·Loida O CasalmeFuyuhiko Matsuda
Jun 3, 2017·Science·Stephen K MurphySeth B Herzon
Jul 1, 2017·Marine Drugs·Taiki UmezawaFuyuhiko Matsuda
Dec 17, 2014·Natural Product Reports·Martin J Schnermann, Ryan A Shenvi
Aug 3, 2011·Natural Product Reports·Braulio M Fraga
Dec 24, 2011·Natural Product Reports·John W BluntMichèle R Prinsep
Nov 18, 2010·Natural Product Reports·Nobuhiro Fusetani
Mar 25, 2017·ACS Medicinal Chemistry Letters·Mary Elisabeth DaubChristopher D Vanderwal
Jul 16, 2011·The Journal of Organic Chemistry·Keisuke NishikawaFuyuhiko Matsuda

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