STUDIES DIRECTED TOWARD THE TOTAL SYNTHESIS OF TETRONOLIDE .1. AN ENANTIOSELECTIVE SYNTHESIS OF THE OCTAHYDRONAPHTHALENE UNIT

被引：31

作者：

BOECKMAN, RK

BARTA, TE

NELSON, SG

机构：

[1] Department of Chemistry University of Rochester, Rochester

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 33期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(00)79871-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient enantioselective route to the octahydronaphthalene unit present in tetronolide (1), the stereochemically complex aglycone common to the tetrocarcins, a novel group of antitumor substances, is described. The sequence employs the intramolecular Diels-Alder reaction to control the relative stereochemistry present on the trans decalin ring system, and incorporates a masked acylating agent which should permit coupling of the two key fragments 2 and 3 as demonstrated by reaction of pentaene 4 with methanol and a model alpha-hydroxy ester.

引用

页码：4091 / 4094

页数：4

共 19 条

[1]

BARTA TE, 1987, THESIS U ROCHESTER

[2] A NEW, HIGHLY EFFICIENT, SELECTIVE METHODOLOGY FOR FORMATION OF MEDIUM-RING AND MACROCYCLIC LACTONES VIA INTRAMOLECULAR KETENE TRAPPING - AN APPLICATION TO A CONVERGENT SYNTHESIS OF (-)-KROMYCIN [J].