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

Chanu Angéline | Zendy; Safir Imad | Zendy; Basak Ramkrishna | Zendy; Chiaroni Angèle | Zendy; Arseniyadis Siméon | Zendy

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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)

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