Literature DB >> 17217299

Enantioselective total synthesis of (+)-gliocladin C.

Larry E Overman1, Youseung Shin.   

Abstract

The first total synthesis of gliocladin C, a fungal-derived marine alkaloid containing a rare trioxopiperazine fragment, is reported. This asymmetric synthesis establishes the absolute configuration of this structurally novel natural product. [reaction: see text].

Entities:  

Mesh：

Substances：

Year:  2007        PMID： 17217299      PMCID： PMC2526118          DOI： 10.1021/ol062801y

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


  6 in total

1.  Novel cytotoxic thiodiketopiperazine derivatives from a Tilachlidium sp.

Authors:  Yunjiang Feng; John W Blunt; Anthony L J Cole; Murray H G Munro
Journal:  J Nat Prod       Date:  2004-12       Impact factor: 4.050

Review 2.  Marine natural products.

Authors:  John W Blunt; Brent R Copp; Murray H G Munro; Peter T Northcote; Michèle R Prinsep
Journal:  Nat Prod Rep       Date:  2006-01-09       Impact factor: 13.423

3.  Nematicidal epipolysulfanyldioxopiperazines from Gliocladium roseum.

Authors:  Jin-Yan Dong; Hong-Ping He; Yue-Mao Shen; Ke-Qin Zhang
Journal:  J Nat Prod       Date:  2005-10       Impact factor: 4.050

4.  Studies on fungal products. IX. Dethiosecoemestrin, a new metabolite related to emestrin, from Emericella striata.

Authors:  H Seya; K Nozawa; S Udagawa; S Nakajima; K Kawai
Journal:  Chem Pharm Bull (Tokyo)       Date:  1986-06       Impact factor: 1.645

5.  Studies on the metabolites of Verticillium sp. structures of Verticillins A, B, and C.

Authors:  H Minato; M Matsumoto; T Katayama
Journal:  J Chem Soc Perkin 1       Date:  1973

6.  Asymmetric construction of quaternary carbon stereocenters: high stereoselection in Mukaiyama aldol reactions of 2-siloxyindoles with chiral aldehydes.

Authors:  Susanta Adhikari; Sebastien Caille; Martin Hanbauer; Vinh X Ngo; Larry E Overman
Journal:  Org Lett       Date:  2005-06-23       Impact factor: 6.005
  6 in total
  15 in total

1.  The palladium catalyzed asymmetric addition of oxindoles and allenes: an atom-economical versatile method for the construction of chiral indole alkaloids.

Authors:  Barry M Trost; Jia Xie; Joshua D Sieber
Journal:  J Am Chem Soc       Date:  2011-11-30       Impact factor: 15.419

Review 2.  Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

Authors:  K C Nicolaou; Christopher R H Hale; Christian Nilewski; Heraklidia A Ioannidou
Journal:  Chem Soc Rev       Date:  2012-06-28       Impact factor: 54.564

3.  Total synthesis of (+)-gliocladin C enabled by visible-light photoredox catalysis.

Authors:  Laura Furst; Jagan M R Narayanam; Corey R J Stephenson
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-12       Impact factor: 15.336

4.  Application of diazene-directed fragment assembly to the total synthesis and stereochemical assignment of (+)-desmethyl-meso-chimonanthine and related heterodimeric alkaloids.

Authors:  Stephen P Lathrop; Mohammad Movassaghi
Journal:  Chem Sci       Date:  2014-01-01       Impact factor: 9.825

5.  Concise Synthesis of (-)-Hodgkinsine, (-)-Calycosidine, (-)-Hodgkinsine B, (-)-Quadrigemine C, and (-)-Psycholeine via Convergent and Directed Modular Assembly of Cyclotryptamines.

Authors:  Petra Lindovska; Mohammad Movassaghi
Journal:  J Am Chem Soc       Date:  2017-11-20       Impact factor: 15.419

6.  Enantioselective total synthesis of plectosphaeroic acid B.

Authors:  Salman Y Jabri; Larry E Overman
Journal:  J Am Chem Soc       Date:  2013-03-06       Impact factor: 15.419

7.  General approach for preparing epidithiodioxopiperazines from trioxopiperazine precursors: enantioselective total syntheses of (+)- and (-)-gliocladine C, (+)-leptosin D, (+)-T988C, (+)-bionectin A, and (+)-gliocladin A.

Authors:  John E DeLorbe; David Horne; Richard Jove; Steven M Mennen; Sangkil Nam; Fang-Li Zhang; Larry E Overman
Journal:  J Am Chem Soc       Date:  2013-03-01       Impact factor: 15.419

8.  A versatile synthesis of unsymmetrical 3,3'-bioxindoles: stereoselective Mukaiyama aldol reactions of 2-siloxyindoles with isatins.

Authors:  J Michael Ellis; Larry E Overman; Huw R Tanner; Jocelyn Wang
Journal:  J Org Chem       Date:  2008-10-15       Impact factor: 4.354

9.  Concise Total Synthesis of (+)-Gliocladins B and C.

Authors:  Nicolas Boyer; Mohammad Movassaghi
Journal:  Chem Sci       Date:  2012-03-30       Impact factor: 9.825

10.  Palladium-catalyzed asymmetric allylic alkylation of 3-aryloxindoles with allylidene dipivalate: a useful enol pivalate product.

Authors:  Barry M Trost; James T Masters; Aaron C Burns
Journal:  Angew Chem Int Ed Engl       Date:  2013-01-17       Impact factor: 15.336
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.