Literature DB >> 17958435

Synthesis and structural reassignment of (+)-epicalyxin F.

Xia Tian1, Scott D Rychnovsky.   

Abstract

We have established the structure of (+)-epicalyxin F through chemical synthesis. An acid-promoted rearrangement of synthetic benzopyran 6 led to the identification of the natural product as (3S,5S,7R)-epicalyxin F (22). Comparison with NMR spectra and optical rotation of the natural product confirms our assignment, and the reassigned structure is compatible with the proposed biosynthetic pathway.

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Year:  2007        PMID： 17958435      PMCID： PMC2496922          DOI： 10.1021/ol702200t

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


  6 in total

1.  Epicalyxin F and calyxin I: two novel antiproliferative diarylheptanoids from the seeds of Alpinia blepharocalyx.

Authors:  M B Gewali; Y Tezuka; A H Banskota; M S Ali; I Saiki; H Dong; S Kadota
Journal:  Org Lett       Date:  1999-12-02       Impact factor: 6.005

2.  Metathesis reactions in total synthesis.

Authors:  K C Nicolaou; Paul G Bulger; David Sarlah
Journal:  Angew Chem Int Ed Engl       Date:  2005-07-18       Impact factor: 15.336

3.  Synthesis and structure revision of calyxin natural products.

Authors:  Xia Tian; James J Jaber; Scott D Rychnovsky
Journal:  J Org Chem       Date:  2006-04-14       Impact factor: 4.354

4.  Eleven novel diarylheptanoids and two unusual diarylheptanoid derivatives from the seeds of Alpinia blepharocalyx.

Authors:  Y Tezuka; M B Gewali; M S Ali; A H Banskota; S Kadota
Journal:  J Nat Prod       Date:  2001-02       Impact factor: 4.050

5.  A facile synthetic approach to prenylated flavanones: first total syntheses of (+/-)-bonannione A and (+/-)-sophoraflavanone A.

Authors:  Y Wang; W Tan; W Z Li; Y Li
Journal:  J Nat Prod       Date:  2001-02       Impact factor: 4.050

6.  A general model for selectivity in olefin cross metathesis.

Authors:  Arnab K Chatterjee; Tae-Lim Choi; Daniel P Sanders; Robert H Grubbs
Journal:  J Am Chem Soc       Date:  2003-09-17       Impact factor: 15.419
  6 in total
  4 in total

1.  Synthesis-guided structure revision of the sarcodonin, sarcoviolin, and hydnellin natural product family.

Authors:  David W Lin; Takeshi Masuda; Moritz B Biskup; Jonathan D Nelson; Phil S Baran
Journal:  J Org Chem       Date:  2011-01-20       Impact factor: 4.354

2.  Manipulating micellar environments for enhancing transition metal-catalyzed cross-couplings in water at room temperature.

Authors:  Bruce H Lipshutz; Subir Ghorai; Wendy Wen Yi Leong; Benjamin R Taft; Daniel V Krogstad
Journal:  J Org Chem       Date:  2011-05-19       Impact factor: 4.354

3.  Formal synthesis of (-)-kendomycin featuring a Prins-cyclization to construct the macrocycle.

Authors:  Kevin B Bahnck; Scott D Rychnovsky
Journal:  J Am Chem Soc       Date:  2008-09-04       Impact factor: 15.419

4.  Evidence for pi-stacking as a source of stereocontrol in the synthesis of the core pyranochromene ring system common to calyxin I, calyxin J, and epicalyxin J.

Authors:  Sidika Polat Cakir; Sean Stokes; Andrzej Sygula; Keith T Mead
Journal:  J Org Chem       Date:  2009-10-02       Impact factor: 4.354
  4 in total

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