Literature DB >> 21247215

The asymmetric Maitland-Japp reaction and its application to the construction of the C1-C19 bis-pyran unit of phorboxazole B.

Paul A Clarke1, Soraia Santos, Nimesh Mistry, Laurence Burroughs, Alexander C Humphries.   

Abstract

The synthesis of the C1-C19 bis-pyran unit of phorboxazole B has been achieved. The key pyran rings were constructed by means of an asymmetric Maitland-Japp reaction and a second Maitland-Japp resolution/cyclization reaction. The longest linear sequence was 14 steps, and the C1-C19 bis-pyran unit was formed in an impressive 10.4% yield.

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Year:  2011        PMID: 21247215     DOI: 10.1021/ol102860r

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


  2 in total

1.  A tandem isomerization/prins strategy: iridium(III)/Brønsted acid cooperative catalysis.

Authors:  Vince M Lombardo; Christopher D Thomas; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2013-11-11       Impact factor: 15.336

Review 2.  Synthesis of the phorboxazoles-potent, architecturally novel marine natural products.

Authors:  Zachary Shultz; James W Leahy
Journal:  J Antibiot (Tokyo)       Date:  2016-03-09       Impact factor: 2.649

  2 in total

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