Organic

Proceedings of the Indian Academy of Sciences - Section A, Chemical Sciences

, Volume 87, Issue 8, pp 239-246

Total synthesis ofdl-9(11)-dehydrotestosterone anddl-testosterone

  • D K BanerjeeAffiliated withDepartment of Organic Chemistry, Indian Institute of Science
  • , K M DamodaranAffiliated withDepartment of Organic Chemistry, Indian Institute of Science
  • , P S N MurthyAffiliated withDepartment of Organic Chemistry, Indian Institute of Science
  • , V PaulAffiliated withDepartment of Organic Chemistry, Indian Institute of Science

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Abstract

17β-Hydroxy-des-A-androst-9-en-5-one (II, R=OH), prepared fromtrans-1β-hydroxy-8-methyl-4, 5-(3′-methyl-4′-methoxybenzo)-hydrindane (I, R=CH3)′, has been converted intodl-9(II)-dehydrotestosterone (IV, R=OH) anddl-testosterone (IX) in very short sequences of steps, albeit in poor yields.

Keywords

Synthesis steroids ring A formation