Synthesis of a Norsesquiterpene Spirolactone/Steroidal Hybrid by Using an Environmentally Friendly Domino Reaction as a Key Step

A new class of hybrid molecules is accessed by elaborating testosterone's AB ring into the norsesquiterpene spirolactone A′B′ ring. The cyclic ene‐acetal 6b, obtained by a PhI(OAc)2‐mediated domino process from vicinal unsaturated diol 5, is used for the synthesis of a norsesquiterpene spirolac...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2007-09, Vol.2007 (26), p.4305-4312
Main Authors: Chanu, Angéline, Safir, Imad, Basak, Ramkrishna, Chiaroni, Angèle, Arseniyadis, Siméon
Format: Article
Language:English
Subjects:
Chemical Sciences
Domino reactions
Hybrid molecules
Iodobenzene diacetate
Lead tetraacetate
Natural products
Organic chemistry
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Summary:A new class of hybrid molecules is accessed by elaborating testosterone's AB ring into the norsesquiterpene spirolactone A′B′ ring. The cyclic ene‐acetal 6b, obtained by a PhI(OAc)2‐mediated domino process from vicinal unsaturated diol 5, is used for the synthesis of a norsesquiterpene spirolactone/testosterone hybrid. The route presented combines the advantages of domino reactions with the ease of functional group interchange on steroidal frameworks. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200700446