Total synthesis of dolabelide D

Journal of the American Chemical Society
Peter K ParkJames L Leighton

Abstract

The first total synthesis of dolabelide D (or of any of the closely related dolabelides) has been achieved with a longest linear sequence of 17 steps. Key features of the synthesis include an application of the catalytic asymmetric silane alcoholysis, the tandem silylformylation-crotylsilylation, and a Brook-like 1,4-carbon to oxygen silyl migration.

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Citations

Apr 29, 2011·Journal of the American Chemical Society·Tyler J HarrisonJames L Leighton
Oct 15, 2009·Journal of the American Chemical Society·K C NicolaouMoumita Kar
May 3, 2011·The Journal of Organic Chemistry·Paul R HansonAlan Whitehead
Jun 29, 2011·The Journal of Organic Chemistry·Sandip P Udawant, Tushar Kanti Chakraborty
May 4, 2011·The Journal of Organic Chemistry·Marie-Gabrielle BraunJoëlle Prunet
Dec 8, 2007·Organic Letters·Joshua D Waetzig, Paul R Hanson
Jan 8, 2009·Organic Letters·Barry M Trost, Andreas Bertogg
Feb 6, 2008·Natural Product Reports·John W BluntMichèle R Prinsep
Jun 3, 2010·Chemical Communications : Chem Comm·Shuo LiTao Ye
Mar 17, 2010·Proceedings of the Japan Academy. Series B, Physical and Biological Sciences·Kiyoyuki YamadaKiyotake Suenaga
Jan 29, 2008·Chemical Society Reviews·Luiz C Dias, Andrea M Aguilar
Feb 5, 2008·Angewandte Chemie·K C NicolaouDavid J Edmonds
Nov 1, 2009·European Journal of Organic Chemistry·Christopher D ThomasPaul R Hanson
Sep 15, 2010·Chemical Society Reviews·Sonia Bracegirdle, Edward A Anderson
Sep 14, 2010·Chemical Communications : Chem Comm·Philipp WinterMathias Christmann
Dec 30, 2020·Marine Drugs·Conxita Avila, Carlos Angulo-Preckler
Oct 22, 2008·Organic Letters·Carles Rodríguez-EscrichJaume Vilarrasa
Jun 5, 2007·Journal of Medicinal Chemistry·Won-Hyuk JungBilly W Day
Dec 5, 2017·Journal of the American Chemical Society·Julie L HofstraSarah E Reisman
Feb 27, 2018·The Journal of Organic Chemistry·Mathilde PantinDaniel P Furkert
Dec 7, 2021·Journal of the American Chemical Society·Xufang LiuQiang Liu

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