Reagent-controlled stereoselective synthesis of lignan-related tetrahydrofurans

The Journal of Organic Chemistry
Steven M MilesWilliam J Coates

Abstract

The reaction of ring-closing metathesis-derived cyclic allylsiloxanes 3 with aldehydes in the presence of a Lewis acid gives 2,3,4-trisubstituted tetrahydrofurans related to the furanolignan family of natural products. The reactions proceed with complete 3,4-trans stereoselectivity, whereas the C-2 stereochemistry depends on both the aldehyde and Lewis acid used. When boron trifluoride etherate is used with aliphatic or electronically neutral aryl aldehydes, the reactions favor the production of the 2,3-cis isomer 8, whereas electron-rich aryl aldehydes lead to the 2,3-trans isomer 9 by Lewis acid-mediated isomerization of the kinetically favored cis isomer. The isomerization can be avoided by use of TMSOTf as a promoter, and hence, the stereochemistry can be tuned by appropriate choice of reagent. Cleavage of the pendant 3-ethenyl group installs the 3-hydroxymethyl group common to the furanolignans.

References

Dec 12, 2001·The Journal of Organic Chemistry·Y Takekawa, K Shishido

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Citations

May 27, 2005·Chemical Communications : Chem Comm·Leticia Jiménez-GonzálezIgnacio Rodríguez-García
Sep 29, 2015·The Journal of Organic Chemistry·Eunhye LeeChan-Mo Yu
Oct 28, 2016·The Journal of Organic Chemistry·Yanrong LiHongjian Lu
May 10, 2017·Angewandte Chemie·Johannes AppunChristoph Schneider
Jan 13, 2015·Organic & Biomolecular Chemistry·Arvind K Yadav, Lal Dhar S Yadav
Sep 6, 2006·Chemistry : a European Journal·Leticia Jiménez-GonzálezIgnacio Rodríguez-García
Feb 23, 2007·Organic & Biomolecular Chemistry·John H CassidyGeoffrey Stemp
Sep 30, 2006·Chemistry : a European Journal·Leticia Jiménez-GonzálezIgnacio Rodríguez-García
Jan 29, 2008·Beilstein Journal of Organic Chemistry·Stephen P Marsden, Alison D McElhinney
Feb 28, 2014·Chemical Communications : Chem Comm·Dong LiuAiwen Lei
Sep 2, 2017·The Journal of Organic Chemistry·Lingling ZhangAiwen Lei

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