Synthesis of (+)-goniothalesdiol and (+)-7-epi-goniothalesdiol

被引：52

作者：

Babjak, M ^{[1
]}

Kapitán, P ^{[1
]}

Gracza, T ^{[1
]}

机构：

[1] Slovak Univ Technol Bratislava, Dept Organ Chem, SK-81237 Bratislava, Slovakia

来源：

TETRAHEDRON | 2005年 / 61卷 / 09期

关键词：

palladium(II) catalysis; stereoselective oxycarbonylation; diastereoselective addition to carbonyl; goniothalesdiol; natural products; PM5; calculations;

D O I：

10.1016/j.tet.2005.01.004

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A total synthesis of (+)-goniothalesdiol, a 3,4-dihydroxy-2,5 -disubstituted tetrahydrofuran isolated from Goniothalamus borneensis (Annonaceae), and its 7-epimer is reported using oxycarbonylation methodology for construction of polyhydroxylated substituted heterocycles. Diastereoselectivity of addition of organometallic reagents to 2,3-O-isopropylidene-D-threose derivatives using theoretical calculations based on the semiempirical PM5 was studied. (C) 2005 Elsevier Ltd. All rights reserved.

引用

页码：2471 / 2479

页数：9

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