Stereoselective synthesis of 8,9-licarinediols

Authors
Nascimento, IR Lopes, LMX Davin, LB Lewis, NG
Citation
Ir. Nascimento et al., Stereoselective synthesis of 8,9-licarinediols, TETRAHEDRON, 56(47), 2000, pp. 9181-9193
Citations number
15
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
47
Year of publication
2000
Pages
9181 - 9193
Database
ISI
SICI code
0040-4020(20001117)56:47<9181:SSO8>2.0.ZU;2-D
Abstract
The total synthesis of 8,9-licarinediols was selectively carried out from l icarin A, previously obtained by oxidative coupling of (E)-isoeugenol. The corresponding enantiomerically pure (+)- and(-)-licarin A ester derivatives were subjected to Sharpless oxidation to yield the asymmetric C-8, C-9 dih ydroxylation products, whose absolute configurations were established by me ans of the CD and NMR spectroscopic analyses of their Mosher ester derivati ves. (C) 2000 Elsevier Science Ltd. All rights reserved.