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Literature DB >> 21028899

Enantioselective synthesis of (-)-sclerophytin A by a stereoconvergent epoxide hydrolysis.

Bin Wang¹, Armando P Ramirez, Justin J Slade, James P Morken.

Abstract

The cytotoxic natural product (-)-sclerophytin A was constructed in 13 steps from geranial. Highlights from the synthesis are a stereoselective Oshima-Utimoto reaction, a Shibata-Baba indium-promoted radical cyclization, and a novel stereoconvergent epoxide hydrolysis.

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Year: 2010 PMID： 21028899 PMCID： PMC3005712 DOI： 10.1021/ja108185z

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

22 in total

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Authors: Stéphane Trudeau; James P Morken
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2. An intramolecular Diels-Alder approach to the eunicellins: enantioselective total syntheses of ophirin B and astrogorgin.

Authors: Michael T Crimmins; Brandon H Brown; Hilary R Plake
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Review 3. Strategies for the total synthesis of C2-C11 cyclized cembranoids.

Authors: J Michael Ellis; Michael T Crimmins
Journal: Chem Rev Date: 2008-12 Impact factor: 60.622

4. Total synthesis of the supposed structure of (-)-sclerophytin A and an improved route to (-)-7-deacetoxyalcyonin acetate.

Authors: L E Overman; L D Pennington
Journal: Org Lett Date: 2000-08-24 Impact factor: 6.005

5. Dihaloindium hydride as a novel reducing agent.

Authors: Akio Baba; Ikuya Shibata
Journal: Chem Rec Date: 2005 Impact factor: 6.771

6. A general strategy for the synthesis of cladiellin diterpenes: enantioselective total syntheses of 6-acetoxycladiell-7(16),11-dien-3-ol (deacetoxyalcyonin acetate), cladiell-11-ene-3,6,7-triol, sclerophytin A, and the initially purported structure of sclerophytin A.

Authors: D W MacMillan; L E Overman; L D Pennington
Journal: J Am Chem Soc Date: 2001-09-19 Impact factor: 15.419

7. Total asymmetric synthesis of the putative structure of the cytotoxic diterpenoid (-)-sclerophytin a and of the authentic natural sclerophytins A and B.

Authors: P Bernardelli; O M Moradei; D Friedrich; J Yang; F Gallou; B P Dyck; R W Doskotch; T Lange; L A Paquette
Journal: J Am Chem Soc Date: 2001-09-19 Impact factor: 15.419

8. Synthesis of the alleged structure of sclerophytin A. The setting of two oxygen bridges within the fused cyclodecanol B ring is not Nature's Way.

Authors: L A Paquette; O M Moradei; P Bernardelli; T Lange
Journal: Org Lett Date: 2000-06-29 Impact factor: 6.005

9. A unified strategy for enantioselective total synthesis of cladiellin and briarellin diterpenes: total synthesis of briarellins E and F and the putative structure of alcyonin and revision of its structure assignment.

Authors: Olivier Corminboeuf; Larry E Overman; Lewis D Pennington
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10. Synthesis and anticancer activity of sclerophytin-inspired hydroisobenzofurans.

Authors: T David Bateman; Aarti L Joshi; Kwangyul Moon; Elena N Galitovskaya; Meenakshi Upreti; Timothy C Chambers; Matthias C McIntosh
Journal: Bioorg Med Chem Lett Date: 2009-10-22 Impact factor: 2.823

3 in total

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2. Total syntheses of (+)-vigulariol and (-)-sclerophytin A.

Authors: Michael T Crimmins; Christina S Stauffer; Mark C Mans
Journal: Org Lett Date: 2011-08-19 Impact factor: 6.005

3. Synthesis and Evaluation of a 2,11-Cembranoid-Inspired Library.

Authors: Amanda J Welford; John J Caldwell; Manjuan Liu; Meirion Richards; Nathan Brown; Cara Lomas; Graham J Tizzard; Mateusz B Pitak; Simon J Coles; Suzanne A Eccles; Florence I Raynaud; Ian Collins
Journal: Chemistry Date: 2016-03-01 Impact factor: 5.236

3 in total