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Synthesis 1993; 1993(10): 957-958
DOI: 10.1055/s-1993-25977
short paper
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Improved Preparation of Enantiomerically Pure (+)-(4aS,5S)-5-tert-Butoxy-4a-methyl-4,4a,5,6,7,8-hexahydro-2(3H)-naphthalenone

Lutz F. Tietze* , Jens Utecht
  • *Institut für Organische Chemie, Universität Göttingen, Tammannstr. 2, D-37 077 Göttingen, Germany
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Publikationsdatum:
29. April 2002 (online)

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(+)-(4aS,5S)-5-tert-Butoxy-4a-methyl-4,4a,5,6,7, 8-hexahydro-2(3H)-naphthalenone (6) is a key intermediate 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 intramolecular aldol condensation of the prochiral trione 2 using catalytic amounts of L-proline, with an ee of 63-70%. Enantiomerically pure 6 was obtained by recrystallization from petroleum ether.