Stereoselective total synthesis of testosterone and androsterone viaA/B-ring construction of the steroidal ring system by intramolecular Diels–Alder reaction
- 1 January 1986
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 1,p. 117-123
- https://doi.org/10.1039/p19860000117
Abstract
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).Keywords
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