AN EFFICIENT ENANTIOSELECTIVE SYNTHESIS OF THE D1 AGONIST 7,11B-HEXAHYDRO-2-PROPYL-3-THIA-5-AZACYCLOPENTA[C] PHENANTHRENE-9,10-DIOL (A-86929)

Authors
EHRLICH PP RALSTON JW MICHAELIDES MR
Citation
Pp. Ehrlich et al., AN EFFICIENT ENANTIOSELECTIVE SYNTHESIS OF THE D1 AGONIST 7,11B-HEXAHYDRO-2-PROPYL-3-THIA-5-AZACYCLOPENTA[C] PHENANTHRENE-9,10-DIOL (A-86929), Journal of organic chemistry, 62(9), 1997, pp. 2782-2785
Citations number
6
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
62
Issue
9
Year of publication
1997
Pages
2782 - 2785
Database
ISI
SICI code
0022-3263(1997)62:9<2782:AEESOT>2.0.ZU;2-G
Abstract
yl-3-thia-5-azacyclopenta[c]phenanthrene-9,10-diol (A-86929, 1), a pot ent selective dopamine D1 agonist, was synthesized enantioselectively from D-aspartic acid. Key features of the 10-step synthesis are the fo llowing: (1) there is no chromatography required; (2) formation of 15 occurs in >99% ee; (3) the electrophilic cyclization to provide the de sired trans stereochemisty in 18 is achieved with no loss of enantiome ric integrity.