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Perkin Transactions 1

Perkin Transactions 1 ceased publication in 2002. Organic & Biomolecular Chemistry is the RSC's journal for high-quality, original organic chemistry research.



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Paper

J. Chem. Soc., Perkin Trans. 1, 1986, 117 - 123, DOI: 10.1039/P19860000117

Stereoselective total synthesis of testosterone and androsterone viaA/B-ring construction of the steroidal ring system by intramolecular Diels–Alder reaction

Masataka Ihara, Izumi Sudow, Keiichiro Fukumoto and Tetsuji Kametani

The optically active indandione (8) was stereoselectively converted into the (E)-triene (23), which was subjected to an intramolecular Diels–Alder reaction to give quantitatively A/B-trans and A/B-cis isomers (24) and (26) in ratios of 4 : 1 and 3.8 : 1. The cycloadduct (24) was transformed into testosterone (4) and androsterone (5).