Mild generation of o-quinone methides. Synthesis of (-)-hexahydrocannabinol and dihydrocannabidiol

Authors
Wang, TS Burgess, JP Reggio, PH Seltzman, HH
Citation
Ts. Wang et al., Mild generation of o-quinone methides. Synthesis of (-)-hexahydrocannabinol and dihydrocannabidiol, SYN COMMUN, 30(8), 2000, pp. 1431-1435
Citations number
20
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNTHETIC COMMUNICATIONS
ISSN journal
00397911 → ACNP
Volume
30
Issue
8
Year of publication
2000
Pages
1431 - 1435
Database
ISI
SICI code
0039-7911(2000)30:8<1431:MGOOMS>2.0.ZU;2-I
Abstract
(-)-Hexahydrocannabinol 7 was synthesized enantioselectively under mild con ditions through the ortho quinone methide mediated cyclization of the adduc t of R-(+)-ciuonellal and the bisethoxyethyl ether of olivetol. The conditi ons enabled the ene product, 1,2-dihydrocannabidiol 6, to be isolated as we ll.