Literature DB >> 18954061

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

Geoff T Halvorsen1, William R Roush.   

Abstract

The synthesis and intramolecular Diels-Alder reactions of trienes 5 and 6 with a siloxacyclopentene-constrained dienophile are described. These reactions provide the primary cycloadducts 7 and 8 with high diastereoselectivity. These cycloadducts possess trans-relationships between the ring fusion proton and the adjacent C(1) alkoxy group and can be further elaborated to alcohols 9 and 11 (via protiodesilylation) or to 10 and 12 (via Fleming-Tamao oxidation) depending on the substitutent R.

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Year:  2008        PMID： 18954061      PMCID： PMC2650085          DOI： 10.1021/ol802266s

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


  8 in total

1.  Studies on the synthesis of (-)-spinosyn a: application of the steric directing group strategy to transannular Diels-Alder reactions.

Authors:  Scott A Frank; William R Roush
Journal:  J Org Chem       Date:  2002-06-14       Impact factor: 4.354

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

Authors:  Dustin J Mergott; Scott A Frank; William R Roush
Journal:  Org Lett       Date:  2002-09-05       Impact factor: 6.005

Review 3.  Recent advances in natural product synthesis by using intramolecular Diels-Alder reactions.

Authors:  Ken-Ichi Takao; Ryosuke Munakata; Kin-ichi Tadano
Journal:  Chem Rev       Date:  2005-12       Impact factor: 60.622

4.  Efficient protiodesilylation of unactivated C(sp3)-SiMe2Ph bonds using tetrabutylammonium fluoride.

Authors:  Cheryl L Heitzman; William T Lambert; Eric Mertz; J Brad Shotwell; Jennifer M Tinsley; Porino Va; William R Roush
Journal:  Org Lett       Date:  2005-06-09       Impact factor: 6.005

5.  Stereochemistry of the allylation and crotylation reactions of alpha-methyl-beta-hydroxy aldehydes with allyl- and crotyltrifluorosilanes. Synthesis of anti,anti-dipropionate stereotriads and stereodivergent pathways for the reactions with 2,3-anti- and 2,3-syn-alpha-methyl-beta-hydroxy aldehydes.

Authors:  Sherry R Chemler; William R Roush
Journal:  J Org Chem       Date:  2003-02-21       Impact factor: 4.354

6.  Unusual Tandem alkynylation and trans-hydrosilylation to form oxasilacyclopentenes.

Authors:  Sarah V Maifeld; Daesung Lee
Journal:  Org Lett       Date:  2005-10-27       Impact factor: 6.005

7.  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

8.  Total synthesis of (-)-spinosyn A: examination of structural features that govern the stereoselectivity of the key transannular Diels-Alder reaction.

Authors:  SusAnn M Winbush; Dustin J Mergott; William R Roush
Journal:  J Org Chem       Date:  2008-01-24       Impact factor: 4.354
  8 in total
  1 in total

1.  Anion relay chemistry: access to the type II ARC reaction manifold through a fundamentally different reaction pathway exploiting 1-oxa-2-silacyclopentanes and related congeners.

Authors:  Amos B Smith; Rongbiao Tong; Won-Suk Kim; William A Maio
Journal:  Angew Chem Int Ed Engl       Date:  2011-08-10       Impact factor: 15.336
  1 in total

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