Construction of spirolactones with concomitant formation of the fused quaternary centre - application to the synthesis of natural products

被引:109
作者
Bartoli, Alexandra [1 ]
Rodier, Fabien [1 ]
Commeiras, Laurent [1 ]
Parrain, Jean-Luc [1 ]
Chouraqui, Gaelle [1 ]
机构
[1] Aix Marseille Univ, Inst Sci Mol Marseille iSm2, UMR CNRS 6263, F-13397 Marseille 20, France
关键词
NEUTRAL SPHINGOMYELINASE INHIBITOR; VINYLOGOUS MANNICH REACTIONS; FREE-RADICAL REACTIONS; SPIRO-GAMMA-LACTONES; PSEUDOARACHNIOTUS-ROSEUS; HETEROCYCLE SYNTHESIS; ASYMMETRIC-SYNTHESIS; EFFICIENT SYNTHESIS; RUGULOVASINE-A; DIMETHYL ACETYLENEDICARBOXYLATE;
D O I
10.1039/c0np00053a
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Polycyclic structures fused at a central carbon are of great interest due to their appealing conformational features and their structural implications in biological systems. Although progress in the development of synthetic methodologies towards such structures has been impressive, the stereoselective construction of such quaternary stereocentres remains a significant challenge in the total synthesis of natural products. This review highlights the progress in the formation of 1-oxaspiro[4.n]alkan-2-ones (2 <= n <= 7) with concomitant formation of the quaternary spiro centre.
引用
收藏
页码:763 / 782
页数:20
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