(1R,2R)-2-(4-Methylenecyclohex-2-enyl)propyl (1R,4S)-camphanate

Citation
F. Korner et al., (1R,2R)-2-(4-Methylenecyclohex-2-enyl)propyl (1R,4S)-camphanate, ACT CRYST C, 56, 2000, pp. 76-77
Citations number
11
Categorie Soggetti
Physical Chemistry/Chemical Physics
Journal title
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS
ISSN journal
01082701 → ACNP
Volume
56
Year of publication
2000
Part
1
Pages
76 - 77
Database
ISI
SICI code
0108-2701(200001)56:<76:((>2.0.ZU;2-A
Abstract
Esterification of a single diastereomer of 2-(4-methylene-cyclohex-2-enyl)p ropanol, (II), with (1R,4S)-(+)-camphanic acid [(1R,4S)-4,7,7-trimethyl-3-o xo-2-oxabicyclo [2.2.1]heptane-1-carboxylic acid] leads to the crystalline title compound, C20H28O4 The relative configuration of the camphanate was d etermined by X-ray diffraction analysis. The outcome clarifies the relative and absolute stereochemistry of the naturally occurring bisabolane sesquit erpenes beta-turmerone and beta-sesquiphellandrene, since we have converted (II) into both natural products via a stereospecific route.