Total synthesis of (+/-)-zearalanone

Authors
Bracher, F Krauss, J
Citation
F. Bracher et J. Krauss, Total synthesis of (+/-)-zearalanone, MONATS CHEM, 132(7), 2001, pp. 805-811
Citations number
16
Categorie Soggetti
Chemistry
Journal title
MONATSHEFTE FUR CHEMIE
ISSN journal
00269247 → ACNP
Volume
132
Issue
7
Year of publication
2001
Pages
805 - 811
Database
ISI
SICI code
0026-9247(200107)132:7<805:TSO(>2.0.ZU;2-K
Abstract
A new approach to the macrocyclic lactone zearalanone is described utilizin g an alkenol and an arene trifluoromethanesulfonate as starting materials. The key step is a Pd(0)-catalyzed cross-coupling of the arene trifluorometh anesulfonate with a 9-alkyl-9-borabicyclo[3.3.1]nonane derived from the alk enol. The title compound is obtained by macrolactonization of a hydroxy aci d under Mitsunobu conditions.