A novel, versatile D-->BCD steroid construction strategy, illustrated by the enantioselective total synthesis of estrone.
A general steroid synthesis is presented that relies on prior formation of three stereogenic centers (C8, C13, and C14) on a D ring template, followed by C- and B-ring cyclizations. The assembly of the key D ring template, achieved by a 3-component conjugate addition/alkylation process, allows introduction of structural variety as required. The method is illustrated by the total synthesis of estrone via a C-ring closing metathesis and a B-ring Heck cyclization.
Foucher
Vincent
V
University of Southampton, School of Chemistry, Highfield, Southampton SO17 1BJ, United Kingdom.
Guizzardi
Benedetta
B
Groen
Marinus B
MB
Light
Mark
M
Linclau
Bruno
B
D000478:Alkylation; D002384:Catalysis; D003500:Cyclization; D004970:Estrone / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D004970:Estrone