Literature DB >> 22711935

Studies on the Synthesis of Reidispongiolide A: Stereoselective Synthesis of the C(22)-C(36) Fragment.

Maben Ying1, William R Roush.   

Abstract

A highly stereoselective synthesis of the C(22)-C(36) fragment 2 of reidispongiolide A is described. This synthesis features the highly stereoselective mismatched double asymmetric crotylboration reaction of the aldehyde derived from 5 and the new chiral reagent (S)-(E)-7 that provides 12 with >15:1 d.r. Subsequent coupling of the derived vinyl iodide 3 with aldehyde 16 provided allylic alcohol 17, that was elaborated by three steps into the targeted reidispongiolide fragment 2.

Entities:  

Year:  2011        PMID： 22711935      PMCID： PMC3375686          DOI： 10.1016/j.tet.2011.10.029

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  16 in total

1.  Total synthesis of (-)-reidispongiolide A, an actin-targeting marine macrolide.

Authors:  Ian Paterson; Kate Ashton; Robert Britton; Giuseppe Cecere; Gaëlle Chouraqui; Gordon J Florence; Jonathan Stafford
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

2.  Actin-binding toxin "tail" wags the dog.

Authors:  Junichi Tanaka; J Craig Blain; John S Allingham
Journal:  Chem Biol       Date:  2008-03

3.  Synthetic mimetics of actin-binding macrolides: rational design of actin-targeted drugs.

Authors:  Richard D Perrins; Giuseppe Cecere; Ian Paterson; Gerard Marriott
Journal:  Chem Biol       Date:  2008-03

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.  Synthesis of enamides related to the salicylate antitumor macrolides using copper-mediated vinylic substitution

Authors: 
Journal:  Org Lett       Date:  2000-05-04       Impact factor: 6.005

6.  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

7.  Enantioselective synthesis of (E)-delta-stannyl homoallylic alcohols via aldehyde allylboration using alpha-stannylallylboranes generated by allene hydroboration followed by a highly diastereoselective 1,3-boratropic shift.

Authors:  Ming Chen; Daniel H Ess; William R Roush
Journal:  J Am Chem Soc       Date:  2010-06-16       Impact factor: 15.419

8.  Synthesis of antimicrofilament marine macrolides: synthesis and configurational assignment of a C5-C16 degradation fragment of reidispongiolide A.

Authors:  Ian Paterson; Robert Britton; Kate Ashton; Henner Knust; Jonathan Stafford
Journal:  Proc Natl Acad Sci U S A       Date:  2004-06-16       Impact factor: 11.205

9.  Toward the synthesis of reidispongiolide a: stereocontrolled synthesis of the C17-C22 and C23-C35 degradation fragments.

Authors:  Ian Paterson; Kate Ashton; Robert Britton; Henner Knust
Journal:  Org Lett       Date:  2003-05-29       Impact factor: 6.005

10.  Copper-mediated synthesis of N-acyl vinylogous carbamic acids and derivatives: synthesis of the antibiotic CJ-15,801.

Authors:  Chong Han; Ruichao Shen; Shun Su; John A Porco
Journal:  Org Lett       Date:  2004-01-08       Impact factor: 6.005
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  7 in total

1.  Total synthesis of (-)-tirandamycin C.

Authors:  Ming Chen; William R Roush
Journal:  Org Lett       Date:  2011-12-07       Impact factor: 6.005

2.  Enantioselective synthesis of (+)-crocacin C. An example of a highly challenging mismatched double asymmetric δ-stannylcrotylboration reaction.

Authors:  Ming Chen; William R Roush
Journal:  Org Lett       Date:  2012-03-12       Impact factor: 6.005

3.  Diastereo- and enantioselective synthesis of (E)-2-Methyl-1,2-syn- and (E)-2-Methyl-1,2-anti-3-pentenediols via allenylboronate kinetic resolution with ((d)Ipc)2BH and aldehyde allylboration.

Authors:  Jeng-Liang Han; Ming Chen; William R Roush
Journal:  Org Lett       Date:  2012-05-30       Impact factor: 6.005

4.  Highly stereoselective synthesis of anti,anti-dipropionate stereotriads: a solution to the long-standing problem of challenging mismatched double asymmetric crotylboration reactions.

Authors:  Ming Chen; William R Roush
Journal:  J Am Chem Soc       Date:  2012-02-14       Impact factor: 15.419

5.  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

6.  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

7.  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
  7 in total

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