A practical synthesis of (E)-2-cyclopentadecen-1-one:: an important precursor of macrocyclic muscone

被引：9

作者：

Hisanaga, Yusuke ^{[1
]}

Asumi, Yuya ^{[1
]}

Takahashi, Masaki ^{[1
]}

Shimizu, Yasuhiro ^{[1
]}

Mase, Nobuyuki ^{[1
]}

Yoda, Hidemi ^{[1
]}

Takabe, Kunihiko ^{[1
]}

机构：

[1] Shizuoka Univ, Fac Engn, Dept Mol Sci, Hamamatsu, Shizuoka 4328561, Japan

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 03期

关键词：

elimination; muscone; macrocycles;

D O I：

10.1016/j.tetlet.2007.11.065

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical synthesis of (E)-2-cyclopentadecen-1-one (E)-2 which is an important precursor of macrocyclic muscone (1) was investigated. Olefination of 2-mesyloxycyclopentadecanone (7c) with strong acid such as sulfuric acid or trifluoromethanesulfonic acid afforded the desired (E)-2 in high yield with extremely high stereo selectivity, which was treated with methylmagnesium cuprate to furnish the dl-muscone in good yield. (C) 2007 Elsevier Ltd. All rights reserved.

引用

页码：548 / 551

页数：4

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