Literature DB >> 21853968

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

Michael T Crimmins1, Christina S Stauffer, Mark C Mans.   

Abstract

The total syntheses of (+)-vigulariol and (-)-sclerophytin A are reported in 15 steps and 16 steps, respectively, from a known compound. The flexible, readily scalable synthetic strategy allows for rapid construction of a critical tricyclic intermediate and is demonstrated via the synthesis of these two marine natural products. A key reaction in this synthetic protocol is a combination Wittig/intramolecular Diels-Alder cycloaddition.
© 2011 American Chemical Society

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Year:  2011        PMID： 21853968      PMCID： PMC3170452          DOI： 10.1021/ol201981j

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  24 in total

1.  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
Journal:  J Am Chem Soc       Date:  2006-02-01       Impact factor: 15.419

Review 2.  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

3.  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

4.  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

5.  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

6.  Application of two-dimensional nmr spectroscopy in the structural determination of marine natural products. Isolation and total structural assignment of 4-deoxyasbestinin diterpenes from the Caribbean gorgonian Briareum asbestinum.

Authors:  J J Morales; D Lorenzo; A D Rodríguez
Journal:  J Nat Prod       Date:  1991 Sep-Oct       Impact factor: 4.050

7.  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

8.  Enantioselective total synthesis of (+)-rogioloxepane A.

Authors:  Michael T Crimmins; Amy C DeBaillie
Journal:  Org Lett       Date:  2003-08-21       Impact factor: 6.005

9.  Structure and absolute configuration of palmonine F, a new eunicellin-based diterpene from the gorgonian Eunicella verrucosa.

Authors:  M J Ortega; E Zubía; J Salva
Journal:  J Nat Prod       Date:  1994-11       Impact factor: 4.050

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

Authors:  Bin Wang; Armando P Ramirez; Justin J Slade; James P Morken
Journal:  J Am Chem Soc       Date:  2010-10-28       Impact factor: 15.419
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  1 in total

Review 1.  Navigating the Chiral Pool in the Total Synthesis of Complex Terpene Natural Products.

Authors:  Zachary G Brill; Matthew L Condakes; Chi P Ting; Thomas J Maimone
Journal:  Chem Rev       Date:  2017-03-15       Impact factor: 60.622
  1 in total

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