Synthesis

Mono-and Bicyclic Cyclopentenes by Rearrangement of 1-Methylcyclobutylmethanols: Synthesis of (±)-Cuparene and Formal Syntheses of (±)-Laurene and (±)- …

K Mandelt, L Fitjer

Index: Mandelt, Klaus; Fitjer, Lutz Synthesis, 1998 , # 10 p. 1523 - 1526

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Citation Number: 15

Abstract

Abstract: Addition of 1-methylcyclobutylmagnesium chloride (3) to acyclic (4d, e) and cyclic ketones (4a–c) yields 1-methylcyclobutylmethanols (5a–e), which may be rearranged to mono-(11–14) and bicyclic cyclopentenes (6–10), respectively. Compounds 11, 12, and 13 are known precursors of (±)-laurene (15),(±)-cuparene (16), and (±)-herbertene (17), respectively. The cyclopentene 11 has been used in a two step synthesis of (±)-cuparene ( ...