Dramatic influence of the substitution of alkylidene-5H-furan-2-ones in Diels-Alder cycloadditions with o-quinonedimethide as diene partner: en route to the CDEF polycyclic ring system of lactonamycin

Organic & Biomolecular Chemistry
Sébastien DuboisJean-Luc Parrain

Abstract

An efficient and rapid synthesis of the CDEF ring system of lactonamycinone is reported via a highly chemo- and diastereoselective intermolecular Diels-Alder cycloaddition between trans-1,2-disilyloxybenzocyclobutene and the appropriate γ-alkylidenebutenolide. The feasibility and the total chemoselectivity of the [4 + 2] cycloaddition for the construction of a spirolactone moiety via an intramolecular approach (IMDA) using both partners is also described demonstrating the versatility of the γ-alkylidenebutenolide building block.

References

Sep 1, 1996·The Journal of Antibiotics·N MatsumotoT Takeuchi
Dec 26, 2001·Chemical Reviews·J L Segura, N Martín
Apr 27, 2002·Organic Letters·T Ross KellyHaixia Wang
Apr 10, 2003·Chemical Reviews·Anil K SadanaW E Billups
Nov 26, 2003·Angewandte Chemie·Tony SiuSamuel J Danishefsky
Mar 16, 2004·The Journal of Antibiotics·Alexandra HöltzelHans-Peter Fiedler
Dec 21, 2004·Organic Letters·T Ross KellyPierre Laurent
Oct 21, 2005·Organic Letters·Barry B Snider, Yefen Zou
Mar 11, 2006·The Journal of Organic Chemistry·David A HendersonAnthony G M Barrett
Oct 10, 2006·The Journal of Organic Chemistry·Hermut WehlanAnthony G M Barrett
Feb 10, 2007·The Journal of Organic Chemistry·Philip J ParsonsJohnathan Board
Aug 14, 2010·The Journal of Organic Chemistry·Kana WatanabeMasaya Nakata
Nov 18, 2010·Natural Product Reports·Nobuhiro Fusetani
Dec 3, 2011·Organic Letters·Alexandra BartoliJean-Luc Parrain

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Citations

Jun 28, 2016·The Journal of Organic Chemistry·Jaime A M AcostaJohn Boukouvalas
Apr 27, 2017·Organic Letters·Philip J ParsonsAndrew J P White
May 11, 2016·Organic & Biomolecular Chemistry·Milandip KarakJohn Boukouvalas
Mar 15, 2014·Physical Chemistry Chemical Physics : PCCP·Jean DrujonJean-Luc Parrain
May 17, 2013·Organic & Biomolecular Chemistry·Fabien RodierLaurent Commeiras
May 30, 2013·Journal of the American Chemical Society·Changchun YuanBo Liu

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