Elsevier

Tetrahedron

Volume 6, Issue 4, 1959, Pages 269-303
Tetrahedron

Selective reactions and modification of functional groups in steroid chemistry

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  • Cited by (59)

    • Traceless bond construction via rearrangement of N-Boc-N-allylhydrazones giving 1,1-disubstituted olefins

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      Both required aldehydes 10a and 10b where synthesized from ergosterol over several steps. 5,6-Dihydroergosterol (8), obtained by hydrogenation of ergosterol in almost quantitative yield,19,20 was oxidized with chromic acid to give 5,6-dihydroergosterone (9a).18 Regioselective ozonolysis of the side chain olefinic group gave the aldehyde 10a in good yield, subsequent condensation with N-Boc-allylhydrazine 5 gave the desired hydrazone 11a.

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