IMPROVED PREPARATION OF ENANTIOMERICALLY PURE THYL-4,4A,5,6,7,8-HEXAHYDRO-2(3H)-NAPHTHALENONE())

Authors
TIETZE LF UTECHT J
Citation
Lf. Tietze et J. Utecht, IMPROVED PREPARATION OF ENANTIOMERICALLY PURE THYL-4,4A,5,6,7,8-HEXAHYDRO-2(3H)-NAPHTHALENONE()), Synthesis, (10), 1993, pp. 957-958
Citations number
25
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthesis → ACNP
ISSN journal
00397881
Issue
10
Year of publication
1993
Pages
957 - 958
Database
ISI
SICI code
0039-7881(1993):10<957:IPOEPT>2.0.ZU;2-S
Abstract
-methyl-4,4a,5,6,7,8-hexahydro-2(3H)-naphthalenone (6) is a key interm ediate in the synthesis of D-homosteroids. Compound 6 was prepared in a five-step sequence via the Wieland-Miescher ketone 4, following the Eder-Sauer-Wiechert-Hajos procedure involving asymmetric intramolecula r aldol condensation of the prochiral trione 2 using catalytic amounts Of L-proline, with an ee of 63 - 70 %. Enantiomerically pure 6 was ob tained by recrystallization from petroleum ether.