BOTPPI, a new Wittig salt for the synthesis of 12-(S)-hydroxy-eicosatetraenoic acid [12-(S)-HETE]

被引：8

作者：

Christiansen, Michael A. ^{[1
,2
]}

Andrus, Merritt B. ^{[1
]}

机构：

[1] Brigham Young Univ, Provo, UT 84602 USA

[2] Utah State Univ, Vernal, UT 84078 USA

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 36期

关键词：

12-(S)-HETE; Wittig; Phase-transfer; Catalysis; Alkylation; PLATELET-TYPE; 12-LIPOXYGENASE; 12-HYDROXYEICOSATETRAENOIC ACID; ARACHIDONIC-ACID; GROWTH-FACTOR; 12(S)-HETE; ANGIOGENESIS; INDUCTION; CYCLOOXYGENASE; PROLIFERATION; PRODUCTS;

D O I：

10.1016/j.tetlet.2012.06.052

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient route to (Z)-(8-benzyloxy-8-oxooct-3-en-1-yl)triphenylphosphonium iodide, or BOTPPI, is disclosed, complete with full experimental details, NMR spectra, and HRMS data. BOTPPI serves as a surrogate for (Z)-(8-methoxy-8-oxooct-3-en-1-yl)triphenylphosphonium iodide, or MOTPPI, a Wittig salt previously used in two 12-HETE syntheses. BOTPPI has the advantage over MOTPPI of being derived from a sequence for which every intermediate is UV-active and amenable to large-scale chromatographic purification. A formal asymmetric total synthesis of 12-(S)-HETE is also reported, involving a stereoselective phase-transfer catalyzed (PTC) alkylation in its key step. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：4805 / 4808

页数：4

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