RuO4-promoted syn-oxidative polycyclization of isoprenoid polyenes:: a new stereoselective cascade process

被引：27

作者：

Bifulco, G

Caserta, T

Gomez-Paloma, L

Piccialli, V

机构：

[1] Univ Naples Federico II, Dipartimento Chim Organ & Biochim, I-80126 Naples, Italy

[2] Univ Salerno, Dipartimento Sci Farmaceut, I-84084 Salerno, Italy

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 50期

关键词：

isoprenoid polyenes; RuO4; oxidative polycyclization; poly-THF; cascade process;

D O I：

10.1016/S0040-4039(02)02304-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Isoprenoid polyenes farnesyl acetate, geranylgeranyl acetate and squalene undergo oxidative polycyclization to bis-, tris-, and penta-tetrahydrofurane products, respectively, in the presence of catalytic amounts of RuO4 (from RuO4.2H(2)O) and NaIO4 as primary oxidant. The stereochemistry of the bis-cyclization product was established as cis-threo-cis-threo through chemical methods and 2D-NMR experiments, and a cascade mechanism was proposed that explains the reactivity exhibited by all the related polyenes. A similarity with rhenium(VII) chemistry has emerged. (C) 2002 Elsevier Science Ltd. All rights reserved.

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收藏

页码：9265 / 9269

页数：5

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