Literature DB >> 22372693

Enantioselective synthesis of (-)-basiliskamide A.

Ming Chen1, William R Roush.   

Abstract

Basiliskamide A is an antifungal polyketide natural product isolated by Andersen and co-workers from a Bacillus laterosporus isolate, PNG-276. A nine-step enantioselective synthesis of (-)-basiliskamide A is reported, starting from commercially available β-hydroxy ester 7. The synthesis features a highly diastereoselective mismatched double asymmetric δ-stannylallylboration reaction of aldehyde 5 with the bifunctional allylborane reagent 4.

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Year:  2012        PMID： 22372693      PMCID： PMC3306514          DOI： 10.1021/ol300282e

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


  10 in total

1.  Catalytic enantioselective addition of allylic organometallic reagents to aldehydes and ketones.

Authors:  Scott E Denmark; Jiping Fu
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

2.  Formal synthesis of (+)-sorangicin A.

Authors:  Michael T Crimmins; Matthew W Haley; Elizabeth A O'Bryan
Journal:  Org Lett       Date:  2011-08-11       Impact factor: 6.005

3.  Stereoselective total synthesis of etnangien and etnangien methyl ester.

Authors:  Pengfei Li; Jun Li; Fatih Arikan; Wiebke Ahlbrecht; Michael Dieckmann; Dirk Menche
Journal:  J Org Chem       Date:  2010-04-16       Impact factor: 4.354

4.  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

5.  Total synthesis of (-)-apicularen A.

Authors:  Sanjay S Palimkar; Jun'ichi Uenishi
Journal:  Org Lett       Date:  2010-09-17       Impact factor: 6.005

6.  Thermodynamic control of 1,3-boratropic shifts of α- and γ-stannyl-substituted allylboranes: hyperconjugation outweighs steric effects.

Authors:  Preston S Stewart; Ming Chen; William R Roush; Daniel H Ess
Journal:  Org Lett       Date:  2011-02-16       Impact factor: 6.005

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.  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

9.  Total synthesis of basiliskamides A and B.

Authors:  Darren J Lipomi; Neil F Langille; James S Panek
Journal:  Org Lett       Date:  2004-09-30       Impact factor: 6.005

10.  Tupuseleiamides and basiliskamides, new acyldipeptides and antifungal polyketides produced in culture by a Bacillus laterosporus isolate obtained from a tropical marine habitat.

Authors:  Todd Barsby; Michael T Kelly; Raymond J Andersen
Journal:  J Nat Prod       Date:  2002-10       Impact factor: 4.050
  10 in total
  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.  (Z)-Selective Takai olefination of salicylaldehydes.

Authors:  Stephen M Geddis; Caroline E Hagerman; Warren R J D Galloway; Hannah F Sore; Jonathan M Goodman; David R Spring
Journal:  Beilstein J Org Chem       Date:  2017-02-20       Impact factor: 2.883
  5 in total

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