CONTROLLING BENZYLIC FUNCTIONALITY AND STEREOCHEMISTRY .1. SYNTHESIS OF THE SECOPSEUDOPTEROSIN AGLYCONE

被引：34

作者：

MCCOMBIE, SW ^{[1
]}

COX, B ^{[1
]}

LIN, SI ^{[1
]}

GANGULY, AK ^{[1
]}

MCPHAIL, AT ^{[1
]}

机构：

[1] DUKE UNIV,PAUL M GROSS CHEM LAB,DURHAM,NC 27706

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 19期

关键词：

D O I：

10.1016/S0040-4039(00)71242-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Directed, homogeneous hydrogenation of 1-(1-hydroxymethylethyl)-5-methoxy-3,4-dihydronaphthalene (7), followed by protection and selective benzylic oxidation gave the 1-oxo-(4R*, 11R*) compound (13). After addition of MeCeCl2, the natural C-1 stereochemistry was established by intramolecular hydride delivery from the di-t-butylsilylether. Final elaboration of the sidechain and the Ar ring substituents gave the secopseudopterosin aglycone ether (3).

引用

页码：2083 / 2086

页数：4

共 17 条

[1] THE APPLICATION OF DIFUNCTIONAL ORGANOSILICON COMPOUNDS TO ORGANIC-SYNTHESIS - 1,3-ASYMMETRIC INDUCTION IN THE REDUCTION OF BETA-HYDROXY-KETONES [J].