Synthetic Study on Stemona Alkaloids. Highly Stereoselective Construction of α-Methyl-γ-lactone Substituted 1-Azabicyclo[5.3.0]decanes

Yoshiki Morimoto; Maki Iwahashi

doi:10.1055/s-1995-5255

Synlett 1995; 1995(12): 1221-1222
DOI: 10.1055/s-1995-5255

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Synthetic Study on Stemona Alkaloids. Highly Stereoselective Construction of α-Methyl-γ-lactone Substituted 1-Azabicyclo[5.3.0]decanes

Yoshiki Morimoto^* , Maki Iwahashi

^*Department of Chemistry, Faculty of Science, Osaka City University, Sumiyoshiku, Osaka 558, Japan

Abstract

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Tricyclic ring system 6, common central structure present in most Stemona alkaloids, was stereoselectively constructed through TMSOTf catalyzed condensation reaction of α-t-butyldioxypyrrolidine 13 with 3-methyl-2-trimethylsilyloxyfuran and subsequent azepane ring formation via intramolecular N-alkylation of iodide 17.

Stemona Alkaloid - 1-Azabicyclo[5.3.0]decane - α-Methyl-γ-lactone - threo-Selective - 3-Methyl-2-trimethylsilyloxyfuran

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