Literature DB >> 20704451

Stereoselective total synthesis of (-)-cleistenolide.

Chao Cai1, Jun Liu, Yuguo Du, Robert J Linhardt.   

Abstract

A facile stereoselective total synthesis of cleistenolide (1) from the natural chiral template d-arabinose has been achieved in eight steps and 49% overall yield, employing key steps including Wittig olefination, selective 1,3-trans-acetal formation, and modified Yamaguchi esterification.

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Year:  2010        PMID： 20704451      PMCID： PMC2921661          DOI： 10.1021/jo101059e

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  6 in total

Review 1.  Annonaceous acetogenins: recent progress.

Authors:  F Q Alali; X X Liu; J L McLaughlin
Journal:  J Nat Prod       Date:  1999-03       Impact factor: 4.050

2.  Constituents from Miliusa balansae (Annonaceae).

Authors:  Christine Kamperdick; Nguyen Hong Van; Tran Van Sung
Journal:  Phytochemistry       Date:  2002-12       Impact factor: 4.072

3.  Enantio- and diastereocontrolled total synthesis of (+)-boronolide.

Authors:  Pradeep Kumar; S Vasudeva Naidu
Journal:  J Org Chem       Date:  2006-05-12       Impact factor: 4.354

4.  Total synthesis of (-)-cleistenolide.

Authors:  Bernd Schmidt; Oliver Kunz; Anne Biernat
Journal:  J Org Chem       Date:  2010-04-02       Impact factor: 4.354

5.  Bioactive constituents of the stem bark of Mitrephora glabra.

Authors:  Chen Li; Dongho Lee; Tyler N Graf; Sharnelle S Phifer; Yuka Nakanishi; Soedarsono Riswan; Fransisca M Setyowati; Achmad M Saribi; Djaja D Soejarto; Norman R Farnsworth; Joseph O Falkinham; David J Kroll; A Douglas Kinghorn; Mansukh C Wani; Nicholas H Oberlies
Journal:  J Nat Prod       Date:  2009-11       Impact factor: 4.050

6.  Solution-phase mixture synthesis with fluorous tagging en route: total synthesis of an eight-member stereoisomer library of passifloricins.

Authors:  Dennis P Curran; Gustavo Moura-Letts; Matthias Pohlman
Journal:  Angew Chem Int Ed Engl       Date:  2006-04-03       Impact factor: 15.336
  6 in total
  1 in total

1.  Synthesis of (S)-FTY720 vinylphosphonate analogues and evaluation of their potential as sphingosine kinase 1 inhibitors and activators.

Authors:  Zheng Liu; Neil MacRitchie; Susan Pyne; Nigel J Pyne; Robert Bittman
Journal:  Bioorg Med Chem       Date:  2013-03-07       Impact factor: 3.641
  1 in total

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