Novel synthesis of highly functionalized 14-beta-hydroxysteroids related to batrachotoxin and ouabain.
The use of anionic polycyclization was investigated in an effort to develop a versatile and convergent synthesis of advanced tetracyclic intermediates of batrachotoxin and ouabain analogues. Two new 5-(trialkylsilyl)-2-cyclohexenones as A ring precursors and a new Nazarov intermediate (D ring precursor) were prepared for this purpose. The reaction of the unsaturated beta-keto aldehyde A ring precursor with the enolate of the Nazarov intermediate afforded, after subsequent transformations, a 14-beta-hydroxysteroid with complete control of stereochemistry.
Trudeau
Stéphane
S
Laboratoire de synthèse organique, Institut de Pharmacologie de Sherbrooke, Université de Sherbrooke, Sherbrooke, Québec J1H 5N4, Canada.
Deslongchamps
Pierre
P
D001496:Batrachotoxins / Q000737:chemistry*; D002316:Cardiotonic Agents / Q000138:chemical synthesis; D003500:Cyclization; D003512:Cyclohexanones / Q000737:chemistry; D006900:Hydroxylation; D006914:Hydroxysteroids / Q000138:chemical synthesis* / Q000737:chemistry; D010042:Ouabain / Q000031:analogs & derivatives*; D013237:Stereoisomerism
D001496:Batrachotoxins; D002316:Cardiotonic Agents; D003512:Cyclohexanones; D006914:Hydroxysteroids; D010042:Ouabain