Literature DB >> 21995677

Concise formal synthesis of (+)-neopeltolide.

Zhen Yang1, Bingbin Zhang, Gaoyuan Zhao, Juan Yang, Xingang Xie, Xuegong She.   

Abstract

A concise formal synthesis of (+)-neopeltolide (1) has been accomplished. The synthesis demonstrated high atom efficiency employing only one step of functional group protection. Key steps involved iridium-catalyzed double asymmetric carbonyl allylation, palladium-catalyzed intramolecular alkoxycarbonylation, ruthenium-catalyzed olefin isomerization, and ring-closing metathesis.
© 2011 American Chemical Society

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Year:  2011        PMID： 21995677     DOI： 10.1021/ol2025718

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


  16 in total

1.  Enantioselective total synthesis of macrolide (+)-neopeltolide.

Authors:  Arun K Ghosh; Khriesto A Shurrush; Zachary L Dawson
Journal:  Org Biomol Chem       Date:  2013-10-11       Impact factor: 3.876

Review 2.  Asymmetric Iridium-Catalyzed C-C Coupling of Chiral Diols via Site-Selective Redox-Triggered Carbonyl Addition.

Authors:  Inji Shin; Michael J Krische
Journal:  Top Curr Chem       Date:  2016

Review 3.  Feedstock Reagents in Metal-Catalyzed Carbonyl Reductive Coupling: Minimizing Preactivation for Efficiency in Target-Oriented Synthesis.

Authors:  Rosalie S Doerksen; Cole C Meyer; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2019-07-26       Impact factor: 15.336

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

Authors:  James M Cabrera; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2019-06-24       Impact factor: 15.336

5.  Catalyst-controlled stereoselective olefin metathesis as a principal strategy in multistep synthesis design: a concise route to (+)-neopeltolide.

Authors:  Miao Yu; Richard R Schrock; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2014-11-06       Impact factor: 15.336

6.  Total synthesis of cyanolide A in the absence of protecting groups, chiral auxiliaries, or premetalated carbon nucleophiles.

Authors:  Andrew R Waldeck; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2013-03-11       Impact factor: 15.336

7.  Strategies and Methods for the Synthesis of Anticancer Natural Product Neopeltolide and its Analogs.

Authors:  Yu Bai; Mingji Dai
Journal:  Curr Org Chem       Date:  2015       Impact factor: 2.180

Review 8.  Catalytic enantioselective C-H functionalization of alcohols by redox-triggered carbonyl addition: borrowing hydrogen, returning carbon.

Authors:  John M Ketcham; Inji Shin; T Patrick Montgomery; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-23       Impact factor: 15.336

Review 9.  Polyketide construction via hydrohydroxyalkylation and related alcohol C-H functionalizations: reinventing the chemistry of carbonyl addition.

Authors:  Anne-Marie R Dechert-Schmitt; Daniel C Schmitt; Xin Gao; Takahiko Itoh; Michael J Krische
Journal:  Nat Prod Rep       Date:  2014-02-11       Impact factor: 13.423

10.  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
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