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
收藏
页码：4712 / 4719
页数：8
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