Literature DB >> 12095319

Tandem intramolecular silylformylation-crotylsilylation: highly efficient synthesis of polyketide fragments.

Michael J Zacuto1, Steven J O'Malley, James L Leighton.   

Abstract

Polyketide fragments may be rapidly and efficiently assembled in the tandem intramolecular silylformylation-crotylsilylation of alkenes and alkynes. The reactions establish up to three new stereocenters with good-to-excellent diastereoselectivity, and the use of the reaction in an iterative sense is demonstrated. In addition, a new dihydrosilane alcoholysis reaction has been developed, leading to a highly efficient sequence.

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Year:  2002        PMID: 12095319     DOI: 10.1021/ja026511y

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  7 in total

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Authors:  Matthew A Horwitz; Jeffrey S Johnson
Journal:  European J Org Chem       Date:  2017-02-07

2.  Total synthesis of dolabelide D.

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Authors:  Tyler J Harrison; Stephen Ho; James L Leighton
Journal:  J Am Chem Soc       Date:  2011-04-27       Impact factor: 15.419

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.  Improved method for the synthesis of beta-carbonyl silyl-1,3-dithianes by the double conjugate addition of 1,3-dithiol to propargylic carbonyl compounds.

Authors:  Sumit Mukherjee; Dimitra Kontokosta; Aditi Patil; Sivakumar Rallapalli; Daesung Lee
Journal:  J Org Chem       Date:  2009-12-04       Impact factor: 4.354

6.  An "aprotic" Tamao oxidation/syn-selective tautomerization reaction for the efficient synthesis of the C1-C9 fragment of fludelone.

Authors:  Tyler J Harrison; Philippe M A Rabbat; James L Leighton
Journal:  Org Lett       Date:  2012-09-05       Impact factor: 6.005

7.  Tandem silylformylation-crotylsilylation/Tamao oxidation of internal alkynes: a remarkable example of generating complexity from simplicity.

Authors:  Jared T Spletstoser; Michael J Zacuto; James L Leighton
Journal:  Org Lett       Date:  2008-12-18       Impact factor: 6.005

  7 in total

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