Literature DB >> 16494476

Total synthesis and stereochemical assignment of the spiroisoxazoline natural product (+)-calafianin.

Sujata Bardhan1, Daniel C Schmitt, John A Porco.   

Abstract

Synthesis of the spiroisoxazoline natural product (+)-calafianin is reported using asymmetric nucleophilic epoxidation and nitrile oxide cycloaddition as key steps. Synthesis and spectral analysis of all calafianin stereoisomers led to unambiguous assignment of relative and absolute stereochemistry.

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Year:  2006        PMID： 16494476     DOI： 10.1021/ol053115m

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


  7 in total

1.  One Pot Spiropyrazoline Synthesis via Intramolecular Cyclization/Methylation.

Authors:  Sureshbabu Dadiboyena; Ashton T Hamme
Journal:  Tetrahedron Lett       Date:  2011-05-18       Impact factor: 2.415

2.  Solid Phase Synthesis of Isoxazole and Isoxazoline-carboxamides via [2+3]-Dipolar Cycloaddition Using Resin-bound Alkynes or Alkenes.

Authors:  Sureshbabu Dadiboyena; Adel Nefzi
Journal:  Tetrahedron Lett       Date:  2012-04-18       Impact factor: 2.415

3.  Construction of Novel Spiroisoxazolines via Intramolecular Cyclization/Methylation.

Authors:  Erick D Ellis; Jianping Xu; Edward J Valente; Ashton T Hamme
Journal:  Tetrahedron Lett       Date:  2009-09-30       Impact factor: 2.415

Review 4.  Recent synthetic studies leading to structural revisions of marine natural products.

Authors:  Yoshihide Usami
Journal:  Mar Drugs       Date:  2009-07-13       Impact factor: 5.118

5.  A Model Study toward the Concise Synthesis of Bromotyrosine Derived Spiroisoxazoline Natural Products and Analogous Core Structures.

Authors:  Prasanta Das; Edward J Valente; Ashton T Hamme
Journal:  European J Org Chem       Date:  2014-05-01

6.  Synthesis and biological evaluation of fluoro-substituted spiro-isoxazolines as potential anti-viral and anti-cancer agents.

Authors:  Prasanta Das; Sarah Boone; Dipanwita Mitra; Lindsay Turner; Ritesh Tandon; Drazen Raucher; Ashton T Hamme
Journal:  RSC Adv       Date:  2020-08-17       Impact factor: 4.036

7.  Inhibition of Oncogenic Transcription Factor REL by the Natural Product Derivative Calafianin Monomer 101 Induces Proliferation Arrest and Apoptosis in Human B-Lymphoma Cell Lines.

Authors:  Alan T Yeo; Spandan Chennamadhavuni; Adrian Whitty; John A Porco; Thomas D Gilmore
Journal:  Molecules       Date:  2015-04-23       Impact factor: 4.411
  7 in total

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