TOTAL SYNTHESIS OF (+)-MONOMORINE I VIA ASYMMETRIC α-KETONIC CLEAVAGE OF 8-AZABICYCLO[3.2.1]OCTAN-3-ONE

• MOMOSE Takefumi

  Faculty of Pharmaceutical Sciences, Toyama Medical & Pharmaceutical University

• TOYOOKA Naoki

  Faculty of Pharmaceutical Sciences, Toyama Medical & Pharmaceutical University

• SEKI Sumie

  Faculty of Pharmaceutical Sciences, Toyama Medical & Pharmaceutical University

• HIRAI Yoshiro

  Faculty of Pharmaceutical Sciences, Toyama Medical & Pharmaceutical University

Abstract

The total synthesis of (+)-monomorine I and preparation of cis-2,5-difunctionalized pyrrolidines, as a chiral synthon, starting with asymmetric cleavage of the 'fork head' ketone of 8-azabicyclo[3.2.1]octan-3-one are described.

Journal

• Chemical & pharmaceutical bulletin

  Chemical & pharmaceutical bulletin 38 (7), 2072-2074, 1990-07-25

  The Pharmaceutical Society of Japan

Keywords

• (+)-monomorine I
• asymmetric α-ketonic cleavage
• 'fork head' ketone
• asymmetric deprotonation
• 8-azabicyclo[3.2.1]octan-3-one
• σ-symmetric bicycic ketone
• ant pheromone
• σ-symmetric pyrrolidine
• ozonolysis

Details

• CRID: 1573668927251101184
• NII Article ID: 110003628715
• NII Book ID: AA00602100
• ISSN: 00092363
• Text Lang: en
• Data Source:
  • CiNii Articles