Versatile Construction of 6-Substituted cis-2,8-Dioxabicyclo[3.3.0]octan-3-ones: Short Enantioselective Total Syntheses of Cheloviolenes A and B and Dendrillolide C

Journal of the American Chemical Society
Yuriy SlutskyyLarry E Overman

Abstract

A short enantioselective synthesis of 6-substituted cis-2,8-dioxabicyclo[3.3.0]octan-3-ones is described. The pivotal step is coupling of a tertiary radical generated directly from a tertiary alcohol with a 3-chloro-5-alkoxybutenolide. This strategy is applied toward scalable 14-15 step syntheses of three rearranged spongian diterpenoids: cheloviolenes A and B and dendrillolide C.

References

Jan 1, 1991·Journal of Natural Products·S C Bobzin, D J Faulkner
Mar 7, 1986·Science·K N HoukR J Loncharich
Feb 3, 2004·Angewandte Chemie·Thomas P BradyEmmanuel A Theodorakis
Sep 24, 2004·Bioorganic & Medicinal Chemistry Letters·Thomas P BradyEmmanuel A Theodorakis
Nov 18, 2005·Organic Letters·Roland WeisserOliver Reiser
Mar 30, 2006·Journal of the American Chemical Society·Gianni GuizzuntiEmmanuel A Theodorakis
Mar 31, 2006·Natural Product Reports·Robert A KeyzersMichael T Davies-Coleman
Mar 2, 2010·Bioorganic & Medicinal Chemistry·Gianni GuizzuntiEmmanuel A Theodorakis
Mar 25, 2010·Proceedings of the National Academy of Sciences of the United States of America·Martin J SchnermannLarry E Overman
Oct 13, 2011·Journal of the American Chemical Society·Martin J SchnermannLarry E Overman
Aug 29, 2012·Angewandte Chemie·Martin J Schnermann, Larry E Overman

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Citations

Aug 14, 2018·Chemical Society Reviews·Kevin J RomeroCorey R J Stephenson
Nov 20, 2018·Angewandte Chemie·Thomas SiemonMathias Christmann
Jan 22, 2019·Natural Product Reports·Anthony R CarrollMichèle R Prinsep
Aug 28, 2019·Chemistry : a European Journal·Francisco José Aguilar TroyanoAdrián Gómez-Suárez
Oct 13, 2018·Chemical Science·Jamie A LeitchDarren J Dixon
Aug 14, 2020·Chemical Reviews·Stefano Crespi, Maurizio Fagnoni
Jul 8, 2021·Chemical Reviews·Spencer P Pitre, Larry E Overman
Sep 5, 2020·Journal of the American Chemical Society·Hao XieXing-Zhong Shu
Jul 21, 2020·Journal of the American Chemical Society·Xinpei CaiMingji Dai
Mar 9, 2018·Chemical Reviews·Lei LiYanxing Jia
Oct 19, 2017·Journal of the American Chemical Society·Satoshi HashimotoMasayuki Inoue
Feb 8, 2018·Journal of the American Chemical Society·Daniel J TaoLarry E Overman
Jul 3, 2019·Accounts of Chemical Research·Xiao-Yu Liu, Yong Qin
Jun 28, 2019·Journal of the American Chemical Society·Kaining ZhangZhiwei Zuo
Dec 20, 2018·Journal of the American Chemical Society·Spencer P PitreLarry E Overman
Dec 29, 2020·Journal of the American Chemical Society·Peng GuoXing-Zhong Shu
Mar 10, 2020·Journal of the American Chemical Society·Durga Prasad HariVarinder K Aggarwal
Nov 6, 2020·Journal of the American Chemical Society·Wei ZhangZhen Yang
Dec 4, 2021·Chemical Reviews·Jennifer L KennemurBenjamin List

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