Synthetic Study on Gymnomitrol and Related Compounds. I.Preparation and Cyclopropane Ring Opening of 1, 2, 6-Trimethyltetracyclo[5.3.1.02, 6.0<8, 11>]undecan-9-one

Takeshi IMANISHI; Yoshimi HIROKAWA; Masayuki YAMASHITA; Tetsuaki TNAKAKA; Kazuyuki MIYASHITA; Chuzo IWATA

doi:10.1248/cpb.41.31

Synthetic Study on Gymnomitrol and Related Compounds. I.Preparation and Cyclopropane Ring Opening of 1, 2, 6-Trimethyltetracyclo[5.3.1.0^{2, 6}.0<8, 11>]undecan-9-one

Takeshi IMANISHI, Yoshimi HIROKAWA, Masayuki YAMASHITA, Tetsuaki TNAKAKA, Kazuyuki MIYASHITA, Chuzo IWATA

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Keywords: cyclopropane cleavage, tetracyclo[5.3.1.0^&glt;2, 6<.0<8, 11>]undecane, Claisen rearrangement, tricyclo[5.3.1.0^{2, 6}]undecane, tricyclo[6.3.0.0^{2, 6}.]undecane, reductive alkylation

JOURNAL FREE ACCESS

1993 Volume 41 Issue 1 Pages 31-35

DOI https://doi.org/10.1248/cpb.41.31

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Abstract

1, 2, 6-Trimethyltetracyclo[5.3.1.0^<2, 6&tg;.0<8, 11>]undecan-9-one (4) was prepared from 1, 5-dimethylbicyclo[3.3.0]octan-3-one (6) in fourteen steps. Its cyclopropane ring opening reaction was examined under various conditions. In all runs, 11-substituted 1, 2, 6-trimethyltricyclo[5.3.1.0^{2, 6}]undecan-9-ones 20 were obtained as major products along with 7-substituted 1, 2, 8-trimethyltricyclo[6.3.0.0<2, 6>]undecan-4-ones 21 and two other products 22 and 23.

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