Literature DB >> 20405855

Enantioselective synthesis of alpha-methylene-beta-hydroxy carboxylic acid derivatives via a diastereoselective aldol/beta-elimination sequence: application to the C(15)-C(21) fragment of tedanolide C.

Roland Barth1, William R Roush.   

Abstract

An enantioselective synthesis of alpha-methylene-beta-hydroxy carboxylic acid derivatives via a highly diastereoselective, one-pot syn-aldol and beta-elimination sequence utilizing the chiral beta-(phenylselenyl)propionyl imide 15 is described. This new method, which constitutes an alternative to the Baylis-Hillman reaction, has been applied to the synthesis of the C(15)-C(21) fragment of tedanolide C.

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Year:  2010        PMID： 20405855      PMCID： PMC2872132          DOI： 10.1021/ol1006955

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


  7 in total

1.  Recent advances in the Baylis-Hillman reaction and applications.

Authors:  Deevi Basavaiah; Anumolu Jaganmohan Rao; Tummanapalli Satyanarayana
Journal:  Chem Rev       Date:  2003-03       Impact factor: 60.622

2.  Structure-activity relationship study on 13-deoxytedanolide, a highly antitumor macrolide from the marine sponge Mycale adhaerens.

Authors:  Shinichi Nishimura; Shigeki Matsunaga; Satoru Yoshida; Yoichi Nakao; Hiroshi Hirota; Nobuhiro Fusetani
Journal:  Bioorg Med Chem       Date:  2005-01-17       Impact factor: 3.641

3.  Recent extensions of the Morita-Baylis-Hillman reaction.

Authors:  Guang-Ning Ma; Jia-Jun Jiang; Min Shi; Yin Wei
Journal:  Chem Commun (Camb)       Date:  2009-08-13       Impact factor: 6.222

4.  Asymmetric allylboration of alpha,beta-enals as a surrogate for the enantioselective synthesis of allylic amines and alpha-amino acids.

Authors:  P Veeraraghavan Ramachandran; Thomas E Burghardt; M Venkat Ram Reddy
Journal:  J Org Chem       Date:  2005-03-18       Impact factor: 4.354

5.  Candidaspongiolides, distinctive analogues of tedanolide from sponges of the genus Candidaspongia.

Authors:  Tamara L Meragelman; Richard H Willis; Girma M Woldemichael; Andrew Heaton; Peter T Murphy; Kenneth M Snader; David J Newman; Rob van Soest; Michael R Boyd; John H Cardellina; Tawnya C McKee
Journal:  J Nat Prod       Date:  2007-06-12       Impact factor: 4.050

6.  Mosher ester analysis for the determination of absolute configuration of stereogenic (chiral) carbinol carbons.

Authors:  Thomas R Hoye; Christopher S Jeffrey; Feng Shao
Journal:  Nat Protoc       Date:  2007       Impact factor: 13.491

7.  Tedanolide C: a potent new 18-membered-ring cytotoxic macrolide isolated from the Papua New Guinea marine sponge Ircinia sp.

Authors:  Camille Chevallier; Tim S Bugni; Xidong Feng; Mary Kay Harper; Anita M Orendt; Chris M Ireland
Journal:  J Org Chem       Date:  2006-03-17       Impact factor: 4.354
  7 in total
  2 in total

1.  Stereochemically versatile synthesis of the C1-C12 fragment of tedanolide C.

Authors:  Thomas E Smith; Sarah J Fink; Zebulon G Levine; Kerani A McClelland; Adrian A Zackheim; Mary E Daub
Journal:  Org Lett       Date:  2012-02-29       Impact factor: 6.005

2.  Enantioselective synthesis of the C1-C11 fragment of tedanolide C.

Authors:  Julie G Geist; Roland Barth; William R Roush
Journal:  Org Lett       Date:  2012-12-18       Impact factor: 6.005
  2 in total

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