Literature DB >> 22703288

Crotylboron-based synthesis of the polypropionate units of chaxamycins A/D, salinisporamycin, and rifamycin S.

Ming Chen1, William R Roush.   

Abstract

Syntheses of the C(15)-C(27) fragments of chaxamycins A/D, rifamycin S, and the C(12)-C(24) fragment of salinisporamycin have been accomplished in 10 steps from commercially available starting materials. Three crotylboron reagents were utilized to construct the seven contiguous stereocenters in these fragments with excellent stereoselectivity.

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Year:  2012        PMID： 22703288      PMCID： PMC3465507          DOI： 10.1021/jo3008226

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  21 in total

Review 1.  Rifamycin-mode of action, resistance, and biosynthesis.

Authors:  Heinz G Floss; Tin-Wein Yu
Journal:  Chem Rev       Date:  2005-02       Impact factor: 60.622

2.  Total synthesis of potential antitumor agent, (-)-dictyostatin.

Authors:  P Veeraraghavan Ramachandran; Amit Srivastava; Debasis Hazra
Journal:  Org Lett       Date:  2007-01-04       Impact factor: 6.005

3.  Formal total synthesis of (-)-saliniketals.

Authors:  J S Yadav; Sk Samad Hossain; Madasu Madhu; Debendra K Mohapatra
Journal:  J Org Chem       Date:  2009-11-20       Impact factor: 4.354

4.  Enantioconvergent hydroboration of a racemic allene: enantioselective synthesis of (E)-δ-stannyl-anti-homoallylic alcohols via aldehyde crotylboration.

Authors:  Ming Chen; William R Roush
Journal:  J Am Chem Soc       Date:  2011-03-30       Impact factor: 15.419

5.  Coupling reactions of cephalosporin sulfones: a stable 3-stannylated cephem.

Authors:  J D Buynak; L Vogeti; H Chen
Journal:  Org Lett       Date:  2001-09-20       Impact factor: 6.005

6.  Streamlined syntheses of (-)-dictyostatin, 16-desmethyl-25,26-dihydrodictyostatin, and 6-epi-16-desmethyl-25,26-dihydrodictyostatin.

Authors:  Wei Zhu; María Jiménez; Won-Hyuk Jung; Daniel P Camarco; Raghavan Balachandran; Andreas Vogt; Billy W Day; Dennis P Curran
Journal:  J Am Chem Soc       Date:  2010-07-07       Impact factor: 15.419

7.  Salinisporamycin, a novel metabolite from Salinispora arenicola. [corrected].

Authors:  Satoru Matsuda; Kyoko Adachi; Yoshihide Matsuo; Manabu Nukina; Yoshikazu Shizuri
Journal:  J Antibiot (Tokyo)       Date:  2009-08-07       Impact factor: 2.649

8.  Total synthesis of (-)-saliniketals A and B.

Authors:  Ian Paterson; Mina Razzak; Edward A Anderson
Journal:  Org Lett       Date:  2008-06-26       Impact factor: 6.005

9.  Inter- and intramolecular differentiation of enantiotopic dioxane acetals through oxazaborolidinone-mediated enantioselective ring-cleavage reaction: kinetic resolution of racemic 1,3-alkanediols and asymmetric desymmetrization of meso-1,3-polyols.

Authors:  Toshiro Harada; Takayuki Egusa; Yasuto Igarashi; Motoharu Kinugasa; Akira Oku
Journal:  J Org Chem       Date:  2002-10-04       Impact factor: 4.354

10.  A concise total synthesis of saliniketal B.

Authors:  Jun Liu; Jef K De Brabander
Journal:  J Am Chem Soc       Date:  2009-09-09       Impact factor: 15.419
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  5 in total

1.  Enantioselective synthesis of (E)-δ-silyl-anti-homoallylic alcohols via an enantiodivergent hydroboration-crotylboration reaction of a racemic allenylsilane.

Authors:  Ming Chen; William R Roush
Journal:  Org Lett       Date:  2013-03-27       Impact factor: 6.005

2.  Enantiodivergent hydroboration reactions of a racemic allenylsilane with diisopinocampheylborane and Curtin-Hammett controlled double asymmetric crotylboration reactions of (S)-E-αphenyldimethylsilyl( d diisopinocampheyl)-crotylborane.

Authors:  Ming Chen; William R Roush
Journal:  Tetrahedron       Date:  2013-09-09       Impact factor: 2.457

3.  Enantiodivergent Hydroboration Reactions of a Racemic Allenylsilane with Diisopinocampheylborane and Curtin-Hammett Controlled Double Asymmetric Crotylboration Reactions of (S)-E-α-phenyldimethylsilyl( d diisopinocampheyl)-crotylborane.

Authors:  Ming Chen; William R Roush
Journal:  Tetrahedron       Date:  2013-07-01       Impact factor: 2.457

4.  Enantioselective synthesis of (Z)- and (E)-2-methyl-1,5-anti-pentenediols via an allene hydroboration-double-allylboration reaction sequence.

Authors:  Ming Chen; William R Roush
Journal:  J Am Chem Soc       Date:  2013-06-12       Impact factor: 15.419

5.  Stereoselective one-pot synthesis of polypropionates.

Authors:  Guo-Ming Ho; Medel Manuel L Zulueta; Shang-Cheng Hung
Journal:  Nat Commun       Date:  2017-09-25       Impact factor: 14.919
  5 in total

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