Literature DB >> 16118878

Oxazoline N-oxide-mediated [2+3] cycloadditions. Application to a synthesis of (-)-tetrahydrolipstatin.

O Dirat1, C Kouklovsky, Y Langlois.   

Abstract

[reaction: see text] A [2+3] cycloaddition of camphor-derived oxazoline N-oxide to alpha,beta-unsaturated ester afforded adduct 8. Tetrahydrolipstatin 1 was prepared from this compound in a nine-step sequence of reactions.

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Year:  1999        PMID： 16118878     DOI： 10.1021/ol990734k

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


  4 in total

1.  A concise, phosphate-mediated approach to the total synthesis of (-)-tetrahydrolipstatin.

Authors:  Phanindra K M Venukadasula; Rambabu Chegondi; Soma Maitra; Paul R Hanson
Journal:  Org Lett       Date:  2010-04-02       Impact factor: 6.005

2.  Synthesis and anticancer activity of new hydroxamic acid containing 1,4-benzodiazepines.

Authors:  Lawrence P Tardibono; Marvin J Miller
Journal:  Org Lett       Date:  2009-04-02       Impact factor: 6.005

3.  Asymmetric synthesis of anti-aldol segments via a nonaldol route: synthetic applications to statines and (-)-tetrahydrolipstatin.

Authors:  Arun K Ghosh; Khriesto Shurrush; Sarang Kulkarni
Journal:  J Org Chem       Date:  2009-06-19       Impact factor: 4.354

4.  Total synthesis of tetrahydrolipstatin and stereoisomers via a highly regio- and diastereoselective carbonylation of epoxyhomoallylic alcohols.

Authors:  Michael Mulzer; Brandon J Tiegs; Yanping Wang; Geoffrey W Coates; George A O'Doherty
Journal:  J Am Chem Soc       Date:  2014-07-18       Impact factor: 15.419
  4 in total

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