Literature DB >> 10602237

Asymmetric Total Synthesis of Fluvirucinine A(1).

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Abstract

Diastereoselective vinyl addition to an amide carbonyl group and amide enolate induced aza-Claisen rearrangement are the key steps in the first asymmetric total synthesis of fluvirucinine A(1) (1), the aglycon of fluvirucin A(1). Fluvirucins are a class of macrolactam antibiotics produced by actinomycete strains that show promising biological properties.

Entities:  

Year:  1999        PMID: 10602237     DOI: 10.1002/(sici)1521-3773(19991203)38:23<3545::aid-anie3545>3.3.co;2-s

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


  6 in total

Review 1.  Natural products as inspiration for the development of asymmetric catalysis.

Authors:  Justin T Mohr; Michael R Krout; Brian M Stoltz
Journal:  Nature       Date:  2008-09-18       Impact factor: 49.962

2.  NICKEL-CATALYZED ASYMMETRIC NEGISHI CROSS-COUPLINGS OF RACEMIC SECONDARY ALLYLIC CHLORIDES WITH ALKYLZINCS: (S,E)-ETHYL 6-(1,3-DIOXOLAN-2-YL)-4-METHYLHEX-2-ENOATE.

Authors:  Sha Lou; Gregory C Fu
Journal:  Organic Synth       Date:  2010-01-01

3.  The palladium-catalyzed anti-Markovnikov hydroalkylation of allylic alcohol derivatives.

Authors:  Ryan J DeLuca; Matthew S Sigman
Journal:  Org Lett       Date:  2012-12-19       Impact factor: 6.005

4.  Lithium hexamethyldisilazide-mediated enolizations: influence of triethylamine on E/Z selectivities and enolate reactivities.

Authors:  Peter F Godenschwager; David B Collum
Journal:  J Am Chem Soc       Date:  2008-06-17       Impact factor: 15.419

5.  Asymmetric Synthesis of (-)-6-Desmethyl-Fluvirucinine A₁ via Conformationally-Controlled Diastereoselective Lactam-Ring Expansions.

Authors:  Hyunyoung Moon; Hojong Yoon; Changjin Lim; Jaebong Jang; Jong-Jae Yi; Jae Kyun Lee; Jeeyeon Lee; Younghwa Na; Woo Sung Son; Seok-Ho Kim; Young-Ger Suh
Journal:  Molecules       Date:  2018-09-14       Impact factor: 4.411

6.  Investigation of Grignard Reagent as an Advanced Base for Aza-Claisen Rearrangement.

Authors:  Bo Reum Song; Min Woo Ha; Donghwan Kim; Chanin Park; Keun Woo Lee; Seung-Mann Paek
Journal:  Molecules       Date:  2019-12-16       Impact factor: 4.411

  6 in total

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