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A novel, versatile D?BCD steroid construction strategy, illustrated by the enantioselective total synthesis of estrone

A novel, versatile D?BCD steroid construction strategy, illustrated by the enantioselective total synthesis of estrone
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.
1523-7060
680-683
Foucher, Vincent
5c33fbe0-3468-4f2f-938a-4349aaabe817
Guizzardi, Benedetta
c5e74eaa-a592-45cb-818a-79686c15baa2
Groen, Marinus B.
0981519a-40fe-4c06-b0a9-9199792e2ae2
Light, Mark
cf57314e-6856-491b-a8d2-2dffc452e161
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Foucher, Vincent
5c33fbe0-3468-4f2f-938a-4349aaabe817
Guizzardi, Benedetta
c5e74eaa-a592-45cb-818a-79686c15baa2
Groen, Marinus B.
0981519a-40fe-4c06-b0a9-9199792e2ae2
Light, Mark
cf57314e-6856-491b-a8d2-2dffc452e161
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba

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).

Record type: Article

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.

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Published date: 22 January 2010

Identifiers

Local EPrints ID: 147899
URI: http://eprints.soton.ac.uk/id/eprint/147899
ISSN: 1523-7060
PURE UUID: e9c8beff-a756-4219-9058-4cd6d30145b2
ORCID for Mark Light: ORCID iD orcid.org/0000-0002-0585-0843
ORCID for Bruno Linclau: ORCID iD orcid.org/0000-0001-8762-0170

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Date deposited: 27 Apr 2010 08:25
Last modified: 07 Oct 2020 07:54

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Contributors

Author: Vincent Foucher
Author: Benedetta Guizzardi
Author: Marinus B. Groen
Author: Mark Light ORCID iD
Author: Bruno Linclau ORCID iD

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