Stereoselective total synthesis of a novel D-homosteroid by a twofold Heckreaction

Authors
Tietze, LF Petersen, S
Citation
Lf. Tietze et S. Petersen, Stereoselective total synthesis of a novel D-homosteroid by a twofold Heckreaction, EUR J ORG C, (9), 2000, pp. 1827-1830
Citations number
38
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
9
Year of publication
2000
Pages
1827 - 1830
Database
ISI
SICI code
1434-193X(200005):9<1827:STSOAN>2.0.ZU;2-1
Abstract
The D-homosteroid 1 was synthesized by two successive Heck reactions starti ng from enantiopure 3 and the bromoarene 2 containing a (Z)-bromovinyl grou p. The first intermolecular Pd-catalyzed reaction leads to 6 in a highly re gio- and diastereoselective way which forms 1 with an unusual cis-junction of the rings B and C by a second intramolecular Heck reaction.