Literature DB >> 34237219

Total Synthesis of Leiodermatolide A via Transfer Hydrogenative Allylation, Crotylation, and Propargylation: Polyketide Construction beyond Discrete Allyl- or Allenylmetal Reagents.

Yuk-Ming Siu1, James Roane1, Michael J Krische1.   

Abstract

The total synthesis of leiodermatolide A was accomplished in 13 steps (LLS). Transfer hydrogenative variants of three carbonyl additions that traditionally rely on premetalated reagents (allylation, crotylation, and propargylation) are deployed together in one total synthesis.

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Year:  2021        PMID： 34237219      PMCID： PMC8529965          DOI： 10.1021/jacs.1c06062

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   16.383


  43 in total

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2.  Natural Products as Sources of New Drugs over the Nearly Four Decades from 01/1981 to 09/2019.

Authors:  David J Newman; Gordon M Cragg
Journal:  J Nat Prod       Date:  2020-03-12       Impact factor: 4.050

Review 3.  Centrosomal Abnormalities in Pancreatic Cancer: Molecular Mechanisms and Clinical Implications.

Authors:  Daniel Ansari; Carolina Del Pino Bellido; Monika Bauden; Roland Andersson
Journal:  Anticancer Res       Date:  2018-03       Impact factor: 2.480

4.  Leiodermatolide, a potent antimitotic macrolide from the marine sponge Leiodermatium sp.

Authors:  Ian Paterson; Stephen M Dalby; Jill C Roberts; Guy J Naylor; Esther A Guzmán; Richard Isbrucker; Tara P Pitts; Pat Linley; Daniela Divlianska; John K Reed; Amy E Wright
Journal:  Angew Chem Int Ed Engl       Date:  2011-03-04       Impact factor: 15.336

Review 5.  Microtubule-binding agents: a dynamic field of cancer therapeutics.

Authors:  Charles Dumontet; Mary Ann Jordan
Journal:  Nat Rev Drug Discov       Date:  2010-10       Impact factor: 84.694

6.  Catalytic Enantioselective Carbonyl Allylation and Propargylation via Alcohol-Mediated Hydrogen Transfer: Merging the Chemistry of Grignard and Sabatier.

Authors:  Seung Wook Kim; Wandi Zhang; Michael J Krische
Journal:  Acc Chem Res       Date:  2017-08-09       Impact factor: 22.384

7.  Enantioselective Alcohol C-H Functionalization for Polyketide Construction: Unlocking Redox-Economy and Site-Selectivity for Ideal Chemical Synthesis.

Authors:  Jiajie Feng; Zachary A Kasun; Michael J Krische
Journal:  J Am Chem Soc       Date:  2016-04-26       Impact factor: 15.419

8.  Leiodermatolide, a novel marine natural product, has potent cytotoxic and antimitotic activity against cancer cells, appears to affect microtubule dynamics, and exhibits antitumor activity.

Authors:  Esther A Guzmán; Qunli Xu; Tara P Pitts; Kaoru Ogawa Mitsuhashi; Cheryl Baker; Patricia A Linley; Judy Oestreicher; Karen Tendyke; Priscilla L Winder; Edward M Suh; Amy E Wright
Journal:  Int J Cancer       Date:  2016-07-19       Impact factor: 7.396

Review 9.  Intermolecular Metal-Catalyzed Reductive Coupling of Dienes, Allenes, and Enynes with Carbonyl Compounds and Imines.

Authors:  Michael Holmes; Leyah A Schwartz; Michael J Krische
Journal:  Chem Rev       Date:  2018-06-13       Impact factor: 60.622

10.  Total synthesis of the antimitotic marine macrolide (-)-leiodermatolide.

Authors:  Ian Paterson; Kenneth K-H Ng; Simon Williams; David C Millican; Stephen M Dalby
Journal:  Angew Chem Int Ed Engl       Date:  2014-01-30       Impact factor: 15.336
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  2 in total

1.  Asymmetric synthesis of aryl/vinyl alkyl carbinol esters via Ni-catalyzed reductive arylation/vinylation of 1-chloro-1-alkanol esters.

Authors:  Deli Sun; Xianghua Tao; Guobin Ma; Jifen Wang; Yunrong Chen
Journal:  Chem Sci       Date:  2022-06-27       Impact factor: 9.969

2.  Proton or Carbene Transfer? On the Dark and Light Reaction of Diazoalkanes with Alcohols.

Authors:  Claire Empel; Chao Pei; Feifei He; Sripati Jana; Rene M Koenigs
Journal:  Chemistry       Date:  2022-02-17       Impact factor: 5.020
  2 in total

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