Literature DB >> 16146398

Synthesis of (+)-bullatacin via the highly diastereoselective [3+2] annulation reaction of a racemic aldehyde and a nonracemic allylsilane.

Jennifer M Tinsley1, Eric Mertz, Pek Y Chong, Robert-André F Rarig, William R Roush.   

Abstract

[reaction: see text] A total synthesis of (+)-bullatacin has been accomplished via a diastereoselective [3+2] annulation reaction of the highly enantiomerically enriched allylsilane 3 and racemic aldehyde 4, which provides the key bis-tetrahydrofuran fragment 15 with > or = 20:1 ds.

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Year:  2005        PMID： 16146398      PMCID： PMC2507730          DOI： 10.1021/ol051719k

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


  21 in total

1.  The first total synthesis of annonacin, the most typical monotetrahydrofuran annonaceous acetogenins.

Authors:  T S Hu; Y L Wu; Y Wu
Journal:  Org Lett       Date:  2000-04-06       Impact factor: 6.005

2.  Total synthesis of cis-solamin.

Authors:  Hidefumi Makabe; Yasunao Hattori; Akira Tanaka; Takayuki Oritani
Journal:  Org Lett       Date:  2002-04-04       Impact factor: 6.005

3.  A convergent total synthesis of (-)-mucocin: an acetogenin from Annonaceae.

Authors:  S Hoppen; S Bäurle; U Koert
Journal:  Chemistry       Date:  2000-07-03       Impact factor: 5.236

4.  Enantioselective total synthesis of (+)-gigantecin: exploiting the asymmetric glycolate aldol reaction.

Authors:  Michael T Crimmins; Jin She
Journal:  J Am Chem Soc       Date:  2004-10-13       Impact factor: 15.419

5.  [3 + 2]-annulation reactions of chiral allylsilanes and chiral aldehydes. studies on the synthesis of bis-tetrahydrofuran substructures of annonaceous acetogenins.

Authors:  Eric Mertz; Jennifer M Tinsley; William R Roush
Journal:  J Org Chem       Date:  2005-09-30       Impact factor: 4.354

6.  Total synthesis of asimicin and bullatacin.

Authors:  H Avedissian; S C Sinha; A Yazbak; A Sinha; P Neogi; S C Sinha; E Keinan
Journal:  J Org Chem       Date:  2000-09-22       Impact factor: 4.354

7.  Total synthesis of the cytotoxic threo, trans, threo, trans, threo annonaceous acetogenin asimin and its C-10 epimer: unambiguous confirmation of absolute stereochemistry.

Authors:  J A Marshall; H Jiang
Journal:  J Nat Prod       Date:  1999-08       Impact factor: 4.050

8.  Total Synthesis of the Cytotoxic Threo, Trans, Erythro, Cis, Threo Annonaceous Acetogenin Trilobin.

Authors:  James A. Marshall; Hongjian Jiang
Journal:  J Org Chem       Date:  1999-02-05       Impact factor: 4.354

9.  Mode of action of bullatacin, a potent antitumor acetogenin: inhibition of NADH oxidase activity of HeLa and HL-60, but not liver, plasma membranes.

Authors:  D J Morré; R de Cabo; C Farley; N H Oberlies; J L McLaughlin
Journal:  Life Sci       Date:  1995       Impact factor: 5.037

10.  Mode of action of bullatacin: a potent antitumor and pesticidal annonaceous acetogenin.

Authors:  K I Ahammadsahib; R M Hollingworth; J P McGovren; Y H Hui; J L McLaughlin
Journal:  Life Sci       Date:  1993       Impact factor: 5.037
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  8 in total

1.  Recent Advances in the Stereoselective Synthesis of Tetrahydrofurans.

Authors:  John P Wolfe; Michael B Hay
Journal:  Tetrahedron       Date:  2007-01-08       Impact factor: 2.457

2.  Enantioselective syntheses of syn- and anti-β-hydroxyallylsilanes via allene hydroboration-aldehyde allylboration reactions.

Authors:  Ming Chen; William R Roush
Journal:  Org Lett       Date:  2011-03-16       Impact factor: 6.005

3.  Total synthesis of amphidinolide E.

Authors:  Porino Va; William R Roush
Journal:  J Am Chem Soc       Date:  2006-12-20       Impact factor: 15.419

4.  Stereoselective synthesis of gamma-substituted (Z)-allylic boranes via kinetically controlled hydroboration of allenes with 10-TMS-9-borabicyclo[3.3.2]decane.

Authors:  Jeremy Kister; Amy C DeBaillie; Ricardo Lira; William R Roush
Journal:  J Am Chem Soc       Date:  2009-10-14       Impact factor: 15.419

5.  Stereoselective syntheses of the C(1)-C(9) fragment of amphidinolide C.

Authors:  Robert H Bates; J Brad Shotwell; William R Roush
Journal:  Org Lett       Date:  2008-09-11       Impact factor: 6.005

6.  Total Synthesis of Amphidinolide E and Amphidinolide E Stereoisomers.

Authors:  Porino Va; William R Roush
Journal:  Tetrahedron       Date:  2007-06-25       Impact factor: 2.457

7.  Diastereoselective synthesis of tetrahydrofurans via mead reductive cyclization of keto-beta-lactones derived from the tandem Mukaiyama aldol lactonization (TMAL) process.

Authors:  T Andrew Mitchell; Daniel Romo
Journal:  J Org Chem       Date:  2007-11-01       Impact factor: 4.354

8.  Recent progress on the total synthesis of acetogenins from Annonaceae.

Authors:  Nianguang Li; Zhihao Shi; Yuping Tang; Jianwei Chen; Xiang Li
Journal:  Beilstein J Org Chem       Date:  2008-12-05       Impact factor: 2.883
  8 in total

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