RuO4-promoted oxidative polycyclization of isoprenoid polyenes.: A further insight into the stereochemistry of the process

被引：25

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 Fisciano, Salerno, Italy

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 29期

关键词：

RuO4; oxidative polycyclization; isoprenoid polyenes; tris-THF configuration; (E; Z)-farnesyl acetate;

D O I：

10.1016/S0040-4039(03)01254-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Further studies on the RuO4-catalyzed oxidative polycyclization of isoprenoid polyenes have been carried out. The configuration of the tris-THF product from the oxidation of geranylgeranyl acetate has been determined by a combination of spectral and chemical correlation methods. The oxidation of (EZ)-farnesyl acetate, synthesized from nerol, has been carried out. This process stops at the first cyclization indicating that an E configuration of the Delta(6) double bond is needed for the second cyclization to occur. The results are discussed in comparison with previous knowledge on the related Re(VII) polycyclization of polyenic bis-homoallylic alcohols. (C) 2003 Elsevier Science Ltd. All rights reserved.

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收藏

页码：5499 / 5503

页数：5

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