Synthesis of an alberta oil sand bitumen C20 tricyclic carboxylic acid bearing a novel diterpenoid skeleton
- 1 January 1988
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 8,p. 2323-2327
- https://doi.org/10.1039/p19880002323
Abstract
The synthesis of (±)-13-norisocopalane-15-carboxylic acid (9), for comparison with the C20 carboxylic acid found in Alberta oil sand bitumen, is described. It involves the preparation of the key intermediate (±)-methyl 16-norisocopalan-l5-oate (27), by transformation of the known allylic alcohol (20), and homologation of (27)via the nitrite (30). Comparison of natural and synthetic methyl ester derivatives unequivocally established the correctness of the structure (9) for the natural product.This publication has 1 reference indexed in Scilit:
- Cationic cyclizations of labda-8(17),12- and labda-8(17),13(16)-dien-14-olThe Journal of Organic Chemistry, 1977