The total synthesis of the cybrodins
- 15 July 1981
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 59 (14) , 2159-2169
- https://doi.org/10.1139/v81-311
Abstract
The total syntheses of cybrodol (1), isocybrodol (2), cybrodal (3), cybrodic acid (4), and trisnorcybrodolide (5), starting from 2-bromomesitylene (6) are described. The route involves oxidation of the 5-methyl group of 6 by means of chromyl acetate, addition of the β-hydroxyethyl chain by aryllithiation and reaction with ethylene oxide, and addition of the fifth carbon substituent by aryllithiation and treatment with ethyl chloroformate to give the key intermediate, methyl 3-(2-hydroxyethyl)-6-methoxymethyl-2,4-dimethylbenzoate (18d). The latter was transformed into trisnorcybrodolide (5), and further elaborated via the corresponding aldehyde 21 into the remaining cybrodins.This publication has 1 reference indexed in Scilit:
- The cybrodins, a new class of sesquiterpenesCanadian Journal of Chemistry, 1981