Open AccessDetermination of the absolute configuration of (−)‐abietic acid via its (4 R ,5 R ,9 R ,10 R )‐7,13‐abietadien‐18‐yl p ‐bromobenzoate derivative
Author(s) -
González Miguel A.,
GilGimeno Maria J.,
Blake Alexander J.
Publication year - 2006
Publication title -
acta crystallographica section e
Language(s) - English
Resource type - Journals
ISSN - 1600-5368
DOI - 10.1107/s1600536806026705
Subject(s) - abietic acid , absolute configuration , chemistry , carbon skeleton , absolute (philosophy) , derivative (finance) , stereochemistry , ring (chemistry) , double bond , organic chemistry , resin acid , philosophy , rosin , epistemology , financial economics , economics
The absolute configuration of the title bromo derivative of abietic acid, C 27 H 35 BrO 2 , has been determined. The structural analysis confirms the absolute stereochemistry for (−)‐abietic acid proposed by Bose & Struck [(1959). Chem. Ind. (London) , pp. 1628–1630] on the basis of optical rotatory dispersion measurements. The molecule exhibits a trans anti 6/6/6 tricyclic hydrocarbon skeleton, with the cyclohexane ring in the expected chair form and the two cyclohexene rings, the double bonds of which are conjugated, in half‐chair conformations.