Total synthesis of (+)- and (-)-duryne: a potent anticancer agent from the marine sponge Cribrochalina dura. Establishment of the central double bond geometry and the absolute configuration of the chiral centers

The Journal of Organic Chemistry
Benjamin W Gung, Ann O Omollo

Abstract

Duryne is a C30 polyacetylenic alcohol with C2 symmetry. Despite its potent cytotoxicity, its central double bond geometry and the absolute configuration of the chiral centers were not determined. We report the total syntheses of both enantiomers of the anticancer natural product (+)-duryne and the establishment of its stereochemistry by synthesizing both geometric isomers. The natural (+)-duryne is identified as (15Z) and (3S,28S) as shown in structure 1. The autoxidation/Wittig coupling reaction was employed to synthesize the central (Z)-olefin. The stereochemistry of the (E)-alkene isomer was constructed stereoselectively by using LiAlH4 reduction of the corresponding alkyne. The absolute configurations of the chiral centers are established by using Burgess' enzymatic resolution procedure with Pseudomonas AK lipase.

References

Jun 28, 2003·Journal of Natural Products·J C BraekmanR W M van Soest
May 11, 2004·The Journal of Organic Chemistry·Benjamin W Gung, Godwin Kumi
Mar 9, 2005·Chemistry : a European Journal·Mary Nell HigleyMarcus Weck

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Citations

May 4, 2011·Journal of Natural Products·Yuki HitoraShigeki Matsunaga
Jul 17, 2013·Journal of Natural Products·Takayuki ShirouzuTomofumi Miyamoto
Dec 20, 2014·Chemical Reviews·Zhen-Fang ZhouYue-Wei Guo
Jan 31, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Roberto MiosoIrma Herrera Bravo de Laguna
Oct 3, 2014·Natural Product Reports·Dymytrii ListunovYves Génisson
Apr 1, 2018·ChemMedChem·Maroua BourkhisYves Génisson
Mar 1, 2009·European Journal of Organic Chemistry·Benjamin W Gung, Ann O Omollo
Jan 30, 2010·Natural Product Reports·John W BluntMichèle R Prinsep
Jul 2, 2010·Natural Product Reports·Jonathan C Morris, Andrew J Phillips
May 30, 2014·Natural Product Reports·Danielle Skropeta, Liangqian Wei

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