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Synthesis of a Norsesquiterpene Spirolactone/Steroidal Hybrid by Using an Environmentally Friendly Domino Reaction as a Key Step
Author(s) -
Chanu Angéline,
Safir Imad,
Basak Ramkrishna,
Chiaroni Angèle,
Arseniyadis Siméon
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700446
Subject(s) - chemistry , domino , environmentally friendly , ring (chemistry) , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , ecology , biology
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)