Literature DB >> 31166641

Total Synthesis of Clavosolide A via Asymmetric Alcohol-Mediated Carbonyl Allylation: Beyond Protecting Groups or Chiral Auxiliaries in Polyketide Construction.

James M Cabrera1, Michael J Krische1.   

Abstract

The 20-membered marine macrodiolide clavosolide A is prepared in 7 steps (LLS) in the absence of protecting groups or chiral auxiliaries via enantioselective alcohol-mediated carbonyl addition. In 9 prior total syntheses, 11-34 steps (LLS) were required.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−C bond formation; enantioselective synthesis; homogenous catalysis; hydrogen transfer; iridium

Year:  2019        PMID： 31166641      PMCID： PMC6656614          DOI： 10.1002/anie.201906259

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  62 in total

1.  Catalytic enantioselective addition of allylic organometallic reagents to aldehydes and ketones.

Authors:  Scott E Denmark; Jiping Fu
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

2.  Total synthesis of a diastereomer of the marine natural product clavosolide A.

Authors:  Conor S Barry; Nick Bushby; Jonathan P H Charmant; Jon D Elsworth; John R Harding; Christine L Willis
Journal:  Chem Commun (Camb)       Date:  2005-09-15       Impact factor: 6.222

Review 3.  Natural products as sources of new drugs over the last 25 years.

Authors:  David J Newman; Gordon M Cragg
Journal:  J Nat Prod       Date:  2007-02-20       Impact factor: 4.050

4.  Total synthesis, structural revision, and absolute configuration of (-)-clavosolide [corrected] A.

Authors:  Jung Beom Son; Si Nae Kim; Na Yeong Kim; Duck Hyung Lee
Journal:  Org Lett       Date:  2006-02-16       Impact factor: 6.005

5.  Clavosolides A and B, dimeric macrolides from the Philippines sponge Myriastra clavosa.

Authors:  M Rama Rao; D John Faulkner
Journal:  J Nat Prod       Date:  2002-03       Impact factor: 4.050

6.  The exceptional chelating ability of dimethylaluminum chloride and methylaluminum dichloride. The merged stereochemical impact of alpha- and beta-stereocenters in chelate-controlled carbonyl addition reactions with enolsilane and hydride nucleophiles.

Authors:  D A Evans; B D Allison; M G Yang; C E Masse
Journal:  J Am Chem Soc       Date:  2001-11-07       Impact factor: 15.419

7.  Total synthesis of (+)-phorboxazole A exploiting the Petasis-Ferrier rearrangement.

Authors:  A B Smith; K P Minbiole; P R Verhoest; M Schelhaas
Journal:  J Am Chem Soc       Date:  2001-11-07       Impact factor: 15.419

8.  Total synthesis of the marine natural product (-)-clavosolide A. A showcase for the Petasis-Ferrier union/rearrangement tactic.

Authors:  Amos B Smith; Vladimir Simov
Journal:  Org Lett       Date:  2006-07-20       Impact factor: 6.005

9.  Total synthesis of the marine natural product (-)-clavosolide A.

Authors:  Conor S Barry; Jon D Elsworth; Peter T Seden; Nick Bushby; John R Harding; Roger W Alder; Christine L Willis
Journal:  Org Lett       Date:  2006-07-20       Impact factor: 6.005

10.  New dimeric macrolide glycosides from the marine sponge Myriastra clavosa.

Authors:  Karen L Erickson; Kirk R Gustafson; Lewis K Pannell; John A Beutler; Michael R Boyd
Journal:  J Nat Prod       Date:  2002-09       Impact factor: 4.050
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  2 in total

Review 1.  Synthetic efforts on the road to marine natural products bearing 4-O-2,3,4,6-tetrasubstituted THPs: an update.

Authors:  Marta Fariña-Ramos; Celina García; Víctor S Martín; Sergio J Álvarez-Méndez
Journal:  RSC Adv       Date:  2021-02-03       Impact factor: 3.361

2.  From Hydrogenation to Transfer Hydrogenation to Hydrogen Auto-Transfer in Enantioselective Metal-Catalyzed Carbonyl Reductive Coupling: Past, Present, and Future.

Authors:  Catherine Gazolla Santana; Michael J Krische
Journal:  ACS Catal       Date:  2021-04-22       Impact factor: 13.084
  2 in total

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