PMID: 11312976Apr 21, 2001Paper

Total synthesis of natural dysidiolide

The Journal of Organic Chemistry
H MiyaokaY Yamada

Abstract

Dysidiolide (1), a novel sesterterpenoid previously isolated from the Caribbean sponge Dysidea etheria de Laubenfels, inhibits the action of the protein phosphatase, cdc25A. The authors establish a novel total synthesis of natural dysidiolide (1) using intramolecular Diels-Alder reaction as the key step from optically active cyclohexenone 3. Decalin, the core structure of 1, was constructed by intramolecular Diels-Alder reaction of the diene ester generated by elimination of the phenyl sulfoxide group from sulfoxide ester 6 prepared from cyclohexenone 3. Diastereoselective methylation at C-7, alkylation at C-6, and deoxygenation of C-12 and C-24 positions gave the fully substituted bicyclic core of 1. The two side chains of the bicyclic core were further extended so as to afford natural dysidiolide (1). The total yield of this synthesis exceeds that of previous syntheses of 1.

References

Sep 29, 2000·Organic Letters·D Demeke, C J Forsyth

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Citations

May 17, 2002·Angewandte Chemie·K C NicolaouGeorgios Vassilikogiannakis
Feb 8, 2006·Chemical & Pharmaceutical Bulletin·Hiroaki MiyaokaHidemichi Mitome
Oct 29, 2002·Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan·Yasuji Yamada
Jul 8, 2015·Organic Letters·Shao-Zheng Peng, Chin-Kang Sha
Oct 7, 2016·Chemical Communications : Chem Comm·Congde HuoFengjuan Chen
Sep 29, 2011·Angewandte Chemie·Pragna Pratic DasJin Kun Cha
Feb 20, 2010·Expert Opinion on Therapeutic Patents·Antonio LavecchiaEttore Novellino
Oct 9, 2012·Organic & Biomolecular Chemistry·Gamal A I MoustafaTakehiko Yoshimitsu
Aug 15, 2014·Natural Product Reports·Veaceslav KulcitkiNicon Ungur
Jun 2, 2012·Natural Product Reports·Daniel T HogDirk Trauner
Feb 28, 2008·Chemical Reviews·Norbert Hoffmann
Jun 22, 2001·Organic Letters·M E Jung, N Nishimura
Sep 13, 2003·The Journal of Organic Chemistry·I S MarcosJ G Urones
Apr 26, 2003·The Journal of Organic Chemistry·Hiroaki MiyaokaYasuji Yamada
Dec 15, 2005·Chemical Reviews·Ken-Ichi TakaoKin-ichi Tadano

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