Studies culminating in the total synthesis and determination of the absolute configuration of (-)-saudin

被引：8

作者：

Boeckman, Robert K., Jr. ^{[1
]}

del Rosario Ferreira, Maria Rico ^{[1
]}

Mitchell, Lorna H. ^{[1
]}

Shao, Pengcheng ^{[1
]}

Neeb, Michael J. ^{[1
]}

Fang, Yue ^{[1
]}

机构：

[1] Univ Rochester, Dept Chem, Rochester, NY 14627 USA

来源：

TETRAHEDRON | 2011年 / 67卷 / 51期

关键词：

Total synthesis; Asymmetric Diels-Alder; Claisen rearrangement; Lewis acid promotion; Stereoselectivity; GENERAL CHIRAL AUXILIARY; STEREOSELECTIVE SYNTHESIS; LITHIUM 2,2,6,6-TETRAMETHYLPIPERIDIDE; CLAISEN REARRANGEMENT; QUATERNARY CENTERS; ACID; ALCOHOLS; STEREOCHEMISTRY; OXIDATION; DIASTEREOSELECTION;

D O I：

10.1016/j.tet.2011.09.067

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A full account of studies that culminated in the total synthesis of both antipodes and the assignment of its absolute configuration of Saudin, a hypoglycemic natural product. Two approaches are described, the first proceeding though bicyclic lactone intermediates and related second monocyclic esters. The former was obtained via asymmetric Diels-Alder cycloaddition and the latter by an asymmetric annulation protocol. Both approaches employ a Lewis acid promoted Claisen rearrangement, with the successful approach taking advantage of bidentate chelation to control the facial selectivity of the key Claisen rearrangement. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：9787 / 9808

页数：22

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