Literature DB >> 16774271

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

Christophe Hoarau1, Thomas R R Pettus.   

Abstract

[reaction: see text] Some selective transformations of resorcinol-derived cyclohexadienone are reported. Efforts led to a structure reported to display anticancer properties. On the basis of the results, the structures for natural products reported to contain a 4,6-dihydroxy-4-alkyl-cyclohexenone nucleus are corrected.

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Year:  2006        PMID： 16774271      PMCID： PMC2440339          DOI： 10.1021/ol061000s

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


  10 in total

1.  Alkyl phenols and derivatives from Tapirira obtusa.

Authors:  S D Correia; J M David; J P David; H B Chai; J M Pezzuto; G A Cordell
Journal:  Phytochemistry       Date:  2001-04       Impact factor: 4.072

2.  Cyclohexadienone ketals and quinols: four building blocks potentially useful for enantioselective synthesis.

Authors:  D Magdziak; S J Meek; T R R Pettus
Journal:  Chem Rev       Date:  2004-03       Impact factor: 60.622

Review 3.  Chasing molecules that were never there: misassigned natural products and the role of chemical synthesis in modern structure elucidation.

Authors:  K C Nicolaou; Scott A Snyder
Journal:  Angew Chem Int Ed Engl       Date:  2005-02-04       Impact factor: 15.336

4.  Two new cytotoxic compounds from Tapirira guianensis.

Authors:  J M David; J P Chávez; H B Chai; J M Pezzuto; G A Cordell
Journal:  J Nat Prod       Date:  1998-02       Impact factor: 4.050

5.  Novel cytotoxic, alkylated hydroquinones from Lannea welwitschii.

Authors:  A Groweiss; J H Cardellina; L K Pannell; D Uyakul; Y Kashman; M R Boyd
Journal:  J Nat Prod       Date:  1997-02       Impact factor: 4.050

Review 6.  Cytotoxic anticancer candidates from natural resources.

Authors:  Jinwoong Kim; Eun Jung Park
Journal:  Curr Med Chem Anticancer Agents       Date:  2002-07

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

Authors:  L H Pettus; R W Van De Water; T R Pettus
Journal:  Org Lett       Date:  2001-03-22       Impact factor: 6.005

8.  Strategies for the Preparation of Differentially Protected ortho-Prenylated Phenols.

Authors:  Christophe Hoarau; Thomas R R Pettus
Journal:  Synlett       Date:  2003       Impact factor: 2.454

9.  Lipoxygenase inhibitory constituents from Periploca aphylla.

Authors:  Aziz-Ur-Rehman Aziz-Ur-Rehman; Abdul Malik; Naheed Riaz; Hafiz Rub Nawaz; Habib Ahmad; Sarfraz Ahmad Nawaz; M Iqbal Choudhary
Journal:  J Nat Prod       Date:  2004-09       Impact factor: 4.050

10.  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
  10 in total
  9 in total

1.  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

2.  A strategy for the late-stage divergent syntheses of scyphostatin analogues.

Authors:  Jacob Y Cha; G Leslie Burnett; Yaodong Huang; Jarrod B Davidson; Thomas R R Pettus
Journal:  J Org Chem       Date:  2011-01-21       Impact factor: 4.354

Review 3.  Dearomatization strategies in the synthesis of complex natural products.

Authors:  Stéphane P Roche; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2011-04-19       Impact factor: 15.336

4.  Enantioselective Synthesis of Hydrobenzofuranones Using an Asymmetric Desymmetrizing Intramolecular Stetter Reaction of Cyclohexadienones.

Authors:  Qin Liu; Tomislav Rovis
Journal:  Org Process Res Dev       Date:  2007       Impact factor: 3.317

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.  Diastereoselective syntheses of chroman spiroketals via [4 + 2] cycloaddition of enol ethers and o-quinone methides.

Authors:  Maurice A Marsini; Yaodong Huang; Christopher C Lindsey; Kun-Liang Wu; Thomas R R Pettus
Journal:  Org Lett       Date:  2008-03-13       Impact factor: 6.005

7.  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

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.  The domestication of ortho-quinone methides.

Authors:  Wen-Ju Bai; Jonathan G David; Zhen-Gao Feng; Marisa G Weaver; Kun-Liang Wu; Thomas R R Pettus
Journal:  Acc Chem Res       Date:  2014-12-03       Impact factor: 22.384
  9 in total

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