Literature DB >> 12201741

Application of the intramolecular vinylogous Morita-Baylis-Hillman reaction toward the synthesis of the spinosyn A tricyclic nucleus.

Dustin J Mergott1, Scott A Frank, William R Roush.   

Abstract

[reaction: see text] A concise synthesis of the spinosyn A tricyclic nucleus 27 has been developed by a route featuring a one-pot tandem intramolecular Diels-Alder reaction and intramolecular vinylogous Morita-Baylis-Hillman cyclization in which five stereocenters in tricycle 10 are set with excellent selectivity.

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Year:  2002        PMID： 12201741     DOI： 10.1021/ol026540d

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


  5 in total

1.  Total synthesis of (-)-spinosyn A.

Authors:  Dustin J Mergott; Scott A Frank; William R Roush
Journal:  Proc Natl Acad Sci U S A       Date:  2004-06-01       Impact factor: 11.205

2.  Remarkable phosphine-effect on the intramolecular aldol reactions of unsaturated 1,5-diketones: highly regioselective synthesis of cross-conjugated dienones.

Authors:  Reema K Thalji; William R Roush
Journal:  J Am Chem Soc       Date:  2005-12-07       Impact factor: 15.419

3.  Siloxacyclopentenes as dienophile-linked directing groups in intramolecular Diels-Alder reactions.

Authors:  Geoff T Halvorsen; William R Roush
Journal:  Org Lett       Date:  2008-10-28       Impact factor: 6.005

4.  Intramolecular Diels-Alder reactions of siloxacyclopentene constrained trienes.

Authors:  Geoff T Halvorsen; William R Roush
Journal:  Org Lett       Date:  2007-05-05       Impact factor: 6.005

5.  Lewis acid-catalyzed conjugate additions of silyloxyallenes: a selective solution to the intermolecular Rauhut-Currier problem.

Authors:  Troy E Reynolds; Michael S Binkley; Karl A Scheidt
Journal:  Org Lett       Date:  2008-05-14       Impact factor: 6.005
  5 in total

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