A novel, versatile D→BCD steroid construction strategy, illustrated by the enantioselective total synthesis of estrone
Foucher, Vincent, Guizzardi, Benedetta, Groen, Marinus B., Light, Mark and Linclau, Bruno (2010) A novel, versatile D→BCD steroid construction strategy, illustrated by the enantioselective total synthesis of estrone. Organic Letters, 12, (4), 680-683. (doi:10.1021/ol902638w).
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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.
|Subjects:||Q Science > QD Chemistry|
|Divisions:||University Structure - Pre August 2011 > School of Chemistry
|Date Deposited:||27 Apr 2010 08:25|
|Last Modified:||25 Apr 2013 22:23|
|Contributors:||Foucher, Vincent (Author)
Guizzardi, Benedetta (Author)
Groen, Marinus B. (Author)
Light, Mark (Author)
Linclau, Bruno (Author)
|Date:||22 January 2010|
|RDF:||RDF+N-Triples, RDF+N3, RDF+XML, Browse.|
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