Literature DB >> 21510632

Stereoselective synthesis of a model C(18)-C(35) spiroketal fragment of integramycin.

Huikai Sun1, Jason R Abbott, William R Roush.   

Abstract

A highly stereoselective synthesis of a model C(18)-C(35) spiroketal unit (7) of integramycin has been accomplished via an enantioselective stannyl-crotylboration reaction and an N-iodosuccinimide-mediated spiroketalization of 19a.

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Year:  2011        PMID： 21510632      PMCID： PMC3094501          DOI： 10.1021/ol200834p

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


  10 in total

Review 1.  HIV integrase structure and function.

Authors:  D Esposito; R Craigie
Journal:  Adv Virus Res       Date:  1999       Impact factor: 9.937

2.  Preparation of the Reagent o-Nitrobenzenesulfonylhydrazide.

Authors:  Andrew G. Myers; Bin Zheng; Mohammad Movassaghi
Journal:  J Org Chem       Date:  1997-10-17       Impact factor: 4.354

Review 3.  HIV integrase, a brief overview from chemistry to therapeutics.

Authors:  R Craigie
Journal:  J Biol Chem       Date:  2001-05-09       Impact factor: 5.157

4.  Synthesis of the C16-C35 fragment of integramycin using olefin hydroesterification as a linchpin reaction.

Authors:  Lijun Wang; Paul E Floreancig
Journal:  Org Lett       Date:  2004-02-19       Impact factor: 6.005

5.  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

6.  Enantioselective Total Synthesis of the Nonisoprenoid Sesquiterpene (-)-Kumausallene.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  1999-11-02       Impact factor: 15.336

7.  Stereoselective synthesis of the octahydronaphthalene unit of integramycin via an intramolecular Diels-Alder reaction.

Authors:  Thomas A Dineen; William R Roush
Journal:  Org Lett       Date:  2005-03-31       Impact factor: 6.005

8.  Structure, stereochemistry, and biological activity of integramycin, a novel hexacyclic natural product produced by Actinoplanes sp. that inhibits HIV-1 integrase.

Authors:  Sheo B Singh; Deborah L Zink; Brian Heimbach; Olga Genilloud; Ana Teran; Keith C Silverman; Russell B Lingham; Peter Felock; Daria J Hazuda
Journal:  Org Lett       Date:  2002-04-04       Impact factor: 6.005

9.  Reactions of alkenylchromium reagents prepared from alkenyl trifluoromethanesulfonates (triflates) with chromium(II) chloride under nickel catalysis.

Authors:  K Takai; M Tagashira; T Kuroda; K Oshima; K Utimoto; H Nozaki
Journal:  J Am Chem Soc       Date:  1986-09-01       Impact factor: 15.419

10.  A multifaceted phosphate tether: application to the C1-C14 subunit of dolabelides A-D.

Authors:  Joshua D Waetzig; Paul R Hanson
Journal:  Org Lett       Date:  2007-12-07       Impact factor: 6.005
  10 in total
  10 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 enantioselective direct alkylation of arylacetic acids with chiral lithium amides as traceless auxiliaries.

Authors:  Craig E Stivala; Armen Zakarian
Journal:  J Am Chem Soc       Date:  2011-07-15       Impact factor: 15.419

5.  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

6.  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

7.  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

8.  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

9.  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

10.  Synthesis of the spiroketal core of integramycin.

Authors:  Evgeny V Prusov
Journal:  Beilstein J Org Chem       Date:  2013-11-12       Impact factor: 2.883
  10 in total

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