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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Description/Abstract
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.
| Item Type: | Article |
|---|---|
| ISSNs: | 1523-7060 (print) 1523-7052 (electronic) |
| Subjects: | Q Science > QD Chemistry |
| Divisions: | University Structure - Pre August 2011 > School of Chemistry |
| Item ID: | 147899 |
| 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 |
| Status: | Published |
| URI: | http://eprints.soton.ac.uk/id/eprint/147899 |
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