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

…, M Takahashi, Y Shimizu, N Mase, H Yoda, K Takabe

Index: Hisanaga, Yusuke; Asumi, Yuya; Takahashi, Masaki; Shimizu, Yasuhiro; Mase, Nobuyuki; Yoda, Hidemi; Takabe, Kunihiko Tetrahedron Letters, 2008 , vol. 49, # 3 p. 548 - 551

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Citation Number: 8

Abstract

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 stereoselectivity, which was treated with methylmagnesium cuprate to furnish the dl-muscone in good yield.