Literature DB >> 21247077

18O assisted analysis of a γ,δ-epoxyketone cyclization: synthesis of the C16-C28 fragment of ammocidin D.

Stephen T Chau1, Yoichi Hayakawa, Gary A Sulikowski.   

Abstract

The C16-C28 fragment common to the cytotoxic macrolide ammocidin D has been prepared by a stereospecific 5-exo closure of a γ,δ-epoxyketone followed by a rearrangement to a pyran acetal. The reaction pathway was traced by (18)O labeling of the keto carbonyl and observation of (18)O induced (13)C shifts in the pyran acetal product. NMR data of the synthetic C16-C28 fragment compared favorably to the natural product providing support of the assigned stereochemistry.

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Year:  2011        PMID： 21247077      PMCID： PMC3079550          DOI： 10.1021/ol103003f

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


  10 in total

1.  First Desymmetrization of a Centrosymmetric Molecule in Natural Product Synthesis: Preparation of a Key Fragment in the Synthesis of Hemibrevetoxin B This work was supported by the University of Leeds (through a Brotherton Scholarship to J.M.H.) and Pfizer. We are extremely grateful to Professor T. Nakata of the Institute of Physical and Chemical Research (RIKEN), Saitama, Japan, for providing us with the NMR spectra of the epoxide 2, the Royal Society for a grant, and AstraZeneca for strategic research funding.

Authors:  Joanne M. Holland; Mark Lewis; Adam Nelson
Journal:  Angew Chem Int Ed Engl       Date:  2001-11-05       Impact factor: 15.336

2.  Total synthesis of (+)-13-deoxytedanolide.

Authors:  Amos B Smith; Christopher M Adams; Stephanie A Lodise Barbosa; Andrew P Degnan
Journal:  J Am Chem Soc       Date:  2003-01-15       Impact factor: 15.419

3.  Total synthesis and stereochemical assignment of myriaporones 1, 3, and 4.

Authors:  Kristen N Fleming; Richard E Taylor
Journal:  Angew Chem Int Ed Engl       Date:  2004-03-19       Impact factor: 15.336

Review 4.  The development of endo-selective epoxide-opening cascades in water.

Authors:  Christopher J Morten; Jeffery A Byers; Aaron R Van Dyke; Ivan Vilotijevic; Timothy F Jamison
Journal:  Chem Soc Rev       Date:  2009-09-16       Impact factor: 54.564

5.  Ammocidin, a new apoptosis inducer in Ras-dependent cells from Saccharothrix sp. I. Production, isolation and biological activity.

Authors:  R Murakami; T Tomikawa; K Shin-ya; J Shinozaki; T Kajiura; T Kinoshita; A Miyajima; H Seto; Y Hayakawa
Journal:  J Antibiot (Tokyo)       Date:  2001-09       Impact factor: 2.649

6.  Ammocidin, a new apoptosis inducer in ras-dependent cells from Saccharothrix sp. II. Physico-chemical properties and structure elucidation.

Authors:  R Murakami; T Tomikawa; K Shin-ya; J Shinozaki; T Kajiura; H Seto; Y Hayakawa
Journal:  J Antibiot (Tokyo)       Date:  2001-09       Impact factor: 2.649

7.  Myriaporones 1-4, cytotoxic metabolites from the Mediterranean bryozoan Myriapora truncata.

Authors:  Jie-Fei Cheng; Jong-Soo Lee; Ryuichi Sakai; Elizabeth A Jares-Erijman; Maria V Silva; Kenneth L Rinehart
Journal:  J Nat Prod       Date:  2007-02-07       Impact factor: 4.050

8.  Water overcomes methyl group directing effects in epoxide-opening cascades.

Authors:  Christopher J Morten; Timothy F Jamison
Journal:  J Am Chem Soc       Date:  2009-05-20       Impact factor: 15.419

9.  Desymmetrization of a centrosymmetric diepoxide: efficient synthesis of a key intermediate in a total synthesis of hemibrevetoxin B.

Authors:  Joanne M Holland; Mark Lewis; Adam Nelson
Journal:  J Org Chem       Date:  2003-02-07       Impact factor: 4.354

10.  Ammocidins B, C and D, new cytotoxic 20-membered macrolides from Saccharothrix sp. AJ9571.

Authors:  Ryo Murakami; Junko Shinozaki; Takayuki Kajiura; Ikuko Kozone; Motoki Takagi; Kazuo Shin-Ya; Haruo Seto; Yoichi Hayakawa
Journal:  J Antibiot (Tokyo)       Date:  2009-01-30       Impact factor: 2.649
  10 in total

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