MONOCYCLIC AND BICYCLIC CYCLOPENTENES BY REARRANGEMENT OF 1-METHYLCYCLOBUTYLMETHANOLS - SYNTHESIS OF (+ -)-CUPARENE AND FORMAL SYNTHESES OF(+/-)-LAURENE AND (+/-)-HERBERTENE/

Authors
MANDELT K FITJER L
Citation
K. Mandelt et L. Fitjer, MONOCYCLIC AND BICYCLIC CYCLOPENTENES BY REARRANGEMENT OF 1-METHYLCYCLOBUTYLMETHANOLS - SYNTHESIS OF (+ -)-CUPARENE AND FORMAL SYNTHESES OF(+/-)-LAURENE AND (+/-)-HERBERTENE/, Synthesis, (10), 1998, pp. 1523-1526
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthesis → ACNP
ISSN journal
00397881
Issue
10
Year of publication
1998
Pages
1523 - 1526
Database
ISI
SICI code
0039-7881(1998):10<1523:MABCBR>2.0.ZU;2-5
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), resp ectively. The cyclopentene 11 has been used in a two step synthesis of (+/-)-cuparene (16).