STEREOSELECTIVE SYNTHESIS OF STEROIDS AND RELATED COMPOUNDS .5. SYNTHTHESIS OF (+ -)-CHOKOL-A BY A TANDEM MICHAEL-ADDITION DIECKMANN CYCLIZATION/

Authors
GROTH U HALFBRODT W KOHLER T KREYE P
Citation
U. Groth et al., STEREOSELECTIVE SYNTHESIS OF STEROIDS AND RELATED COMPOUNDS .5. SYNTHTHESIS OF (+ -)-CHOKOL-A BY A TANDEM MICHAEL-ADDITION DIECKMANN CYCLIZATION/, Liebigs Annalen der Chemie, (9), 1994, pp. 885-890
Citations number
32
Categorie Soggetti
Chemistry
Journal title
Liebigs Annalen der Chemie → ACNP
ISSN journal
01702041
Issue
9
Year of publication
1994
Pages
885 - 890
Database
ISI
SICI code
0170-2041(1994):9<885:SSOSAR>2.0.ZU;2-0
Abstract
A total synthesis of (+/-)-chokol A (rac-12) was accomplished in five steps by starting from the alpha,beta-unsaturated ester (E)-2 in an ov erall yield of 24%. The key step of this synthesis is the tandem conju gate addition/Dieckmann cyclization of the cuprate derived from vinyl bromide 9 with the alpha,beta-unsaturated ester (E)-2.