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

Takefumi MOMOSE; Naoki TOYOOKA; Sumie SEKI; Yoshiro HIRAI

doi:10.1248/cpb.38.2072

Takefumi MOMOSE, Naoki TOYOOKA, Sumie SEKI, Yoshiro HIRAI

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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

JOURNAL FREE ACCESS

1990 Volume 38 Issue 7 Pages 2072-2074

DOI https://doi.org/10.1248/cpb.38.2072

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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.

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