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Diversity-oriented synthesis of enantiomerically pure steroidal tetracycles employing Stille/Diels-Alder reaction sequences

Sunnemann, Hans Wolf; Banwell, Martin; de Meijere, Armin

Description

Various steroid analogues were synthesized by Stille coupling of bicyclo[4.3.0]nonenylstannanes cis-/trans-8 and 14 with cyclohexenol triflates 17 and 18 and subsequent Diels-Alder reactions of the resulting dienes. The enantiomerically pure bicyclo[4.3.0]nonenylstannanes cis- and trans-8 were prepared in good yields via the enol triflates cis- and trans-7, obtained from the bicyclo[4.3.0]non-2-en-3-one 5. The alkenylstannane 14 was obtained from the [2+2] cycloadduct 10a produced from addition...[Show more]

CollectionsANU Research Publications
Date published: 2008
Type: Journal article
URI: http://hdl.handle.net/1885/52112
Source: Chemistry, A European Journal
DOI: 10.1002/chem.200800601

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