Literature DB >> 11263912

Synthesis of (+/-)-epoxysorbicillinol using a novel cyclohexa-2,5-dienone with synthetic applications to other sorbicillin derivatives.

L H Pettus1, R W Van De Water, T R Pettus.   

Abstract

A novel route to epoxysorbicillinol as well as dimers of sorbicillin is reported. The synthesis is-in principle-amenable to enantioselectivity. The key step is an oxidative dearomatization to produce a stable and highly malleable p-quinol intermediate, which undergoes a highly diastereoselective epoxidation.

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Year:  2001        PMID： 11263912      PMCID： PMC1360178          DOI： 10.1021/ol0155438

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


  5 in total

1.  Photochemical and Acid-Catalyzed Rearrangements of 4-Carbomethoxy-4-methyl-3-(trimethylsilyl)-2,5-cyclohexadien-1-one.

Authors:  Arthur G. Schultz; Evan G. Antoulinakis
Journal:  J Org Chem       Date:  1996-07-12       Impact factor: 4.354

2.  A two-step total synthesis of the natural pentacycle trichodimerol, a novel inhibitor of TNF-alpha production.

Authors:  D Barnes-Seeman; E J Corey
Journal:  Org Lett       Date:  1999-11-04       Impact factor: 6.005

3.  BMS-182123, a fungal metabolite that inhibits the production of TNF-alpha by macrophages and monocytes.

Authors:  G A Warr; J A Veitch; A W Walsh; G A Hesler; D M Pirnik; J E Leet; P F Lin; I A Medina; K D McBrien; S Forenza; J M Clark; K S Lam
Journal:  J Antibiot (Tokyo)       Date:  1996-03       Impact factor: 2.649

4.  Trichodimerol (BMS-182123) inhibits lipopolysaccharide-induced eicosanoid secretion in THP-1 human monocytic cells.

Authors:  C E Mazzucco; G Warr
Journal:  J Leukoc Biol       Date:  1996-08       Impact factor: 4.962

5.  Biomimetic Explorations Towards the Bisorbicillinoids: Total Synthesis of Bisorbicillinol, Bisorbibutenolide, and Trichodimerol.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  1999-12-03       Impact factor: 15.336
  5 in total
  9 in total

1.  General synthesis for chiral 4-alkyl-4-hydroxycyclohexenones.

Authors:  Christophe Hoarau; Thomas R R Pettus
Journal:  Org Lett       Date:  2006-06-22       Impact factor: 6.005

2.  Total synthesis of (+)-rishirilide B: development and application of general processes for enantioselective oxidative dearomatization of resorcinol derivatives.

Authors:  Lupe H Mejorado; Thomas R R Pettus
Journal:  J Am Chem Soc       Date:  2006-12-13       Impact factor: 15.419

3.  Regioselective oxidation of phenols to o-quinones with o-iodoxybenzoic acid (IBX).

Authors:  Derek Magdziak; Andy A Rodriguez; Ryan W Van De Water; Thomas R R Pettus
Journal:  Org Lett       Date:  2002-01-24       Impact factor: 6.005

4.  Chemoselective Epoxidation of Electron Deficient Enones with Iodosylbenzene.

Authors:  Kevin M McQuaid; Thomas R R Pettus
Journal:  Synlett       Date:  2004-11-03       Impact factor: 2.454

5.  Total synthesis of TK-57-164A, isariotin F, and their putative progenitor isariotin E.

Authors:  Jacob Y Cha; Yaodong Huang; Thomas R R Pettus
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

6.  Enantioselective total synthesis of all of the known chiral cleroindicins (C-F): clarification among optical rotations and assignments.

Authors:  Todd A Wenderski; Shenlin Huang; Thomas R R Pettus
Journal:  J Org Chem       Date:  2009-06-05       Impact factor: 4.354

7.  Diastereoselective dearomatization of resorcinols directed by a lactic acid tether: unprecedented enantioselective access to p-quinols.

Authors:  Lupe H Mejorado; Christophe Hoarau; Thomas R R Pettus
Journal:  Org Lett       Date:  2004-05-13       Impact factor: 6.005

8.  Dearomatization applications of I(III) reagents and some unusual reactivity amongst resorcinol derived cyclohexadienones.

Authors:  Todd A Wenderski; Christophe Hoarau; Lupe Mejorado; Thomas R R Pettus
Journal:  Tetrahedron       Date:  2010-07       Impact factor: 2.457

9.  Biocatalytic site- and enantioselective oxidative dearomatization of phenols.

Authors:  Summer A Baker Dockrey; April L Lukowski; Marc R Becker; Alison R H Narayan
Journal:  Nat Chem       Date:  2017-11-13       Impact factor: 24.427
  9 in total

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