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

被引：21

作者：

Dubois, Sebastien ^{[1
]}

Rodier, Fabien ^{[1
]}

Blanc, Romain ^{[1
]}

Rahmani, Raphael ^{[1
]}

Heran, Virginie ^{[1
]}

Thibonnet, Jerome ^{[2
]}

Commeiras, Laurent ^{[1
]}

Parrain, Jean-Luc ^{[1
]}

机构：

[1] Aix Marseille Univ, Inst Sci Mol Marseille iSm2, UMR 7313, F-13397 Marseille 20, France

[2] Univ Tours, Dept Chim, Lab PCMB, F-37200 Tours, France

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2012年 / 10卷 / 24期

关键词：

MARINE VERRUCOSISPORA STRAIN; ASYMMETRIC-SYNTHESIS; BIRADICAL MECHANISM; SITE SELECTIVITY; ABYSSOMICIN-C; MODEL; CONSTRUCTION; 5-METHYLENE-2(5H)-FURANONES; PROTOANEMONIN; DERIVATIVES;

D O I：

10.1039/c2ob25299f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 gamma-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 gamma-alkylidenebutenolide building block.

引用

页码：4712 / 4719

页数：8

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