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Communication | Special issue | Vol 10, No. 1, 1978, pp.207-220
Published online, 1st January, 1970
DOI: 10.3987/S-1978-01-0207
Synthesis of A-Thienosteroids and Related Compounds

Taichiro Komeno,* Hikozo Iwakura, and Ken’ichi Takeda

*Shionogi Research Laboratories, Shionogi & Co. Ltd., Fukushima-ku, Osaka 553-0002, Japan

Abstract

The Grignard reaction of optically active 1,5-dioxo-7α-methyl-3aα,7aβ-hexahydroindan-4α-yl acetic acid with 2- and 3-thienyl magnesium bromide, followed by lactonization gave thienyl γ-lactones, 8a and 8b, respectively. Their configurations were established by the dipole moments. They were converted through multi-steps to a number of A-thienosteroids, namely modified steroids in which the ring A are displaced by fused thiophenes. A-thiolenone derivatives also were prepared from these A-thienosteroids.