Issue 24, 2010

Diels–Alder cycloaddition of o-quinonedimethides and alkylidene-5H-furan-2-ones: new and rapid access to lambertellol cores and arthrinone derivatives

Abstract

An efficient synthesis of deoxy-lambertellols was reported through a highly chemo- and diastereoselective intermolecular Diels–Alder cycloaddition between trans-1,2-disiloxybenzocyclobutenes and 2-methylprotoanemonine. Such transformation with δ-substituted γ-alkylidenebutenolides, to prepare new analogues of these tricyclic spirolactones, which would be very difficult to prepare by other ways, was also studied.

Graphical abstract: Diels–Alder cycloaddition of o-quinonedimethides and alkylidene-5H-furan-2-ones: new and rapid access to lambertellol cores and arthrinone derivatives

Supplementary files

Article information

Article type
Communication
Submitted
19 Jul 2010
Accepted
16 Sep 2010
First published
08 Oct 2010

Org. Biomol. Chem., 2010,8, 5490-5494

Diels–Alder cycloaddition of o-quinonedimethides and alkylidene-5H-furan-2-ones: new and rapid access to lambertellol cores and arthrinone derivatives

R. Blanc, V. Héran, R. Rahmani, L. Commeiras and J. Parrain, Org. Biomol. Chem., 2010, 8, 5490 DOI: 10.1039/C0OB00448K

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