Literature DB >> 19795876

A synthesis of the carbon skeleton of maoecrystal V.

Paul J Krawczuk1, Niklas Schöne, Phil S Baran.   

Abstract

An enantioselective synthesis of the maoecrystal V (1) carbon skeleton is described. The key transformations include arylation of a 1,3-dicarbonyl compound with a triarylbismuth(V) dichloride species, oxidative dearomatization of a phenol, and a subsequent intramolecular Diels-Alder reaction.

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Year:  2009        PMID： 19795876      PMCID： PMC2783297          DOI： 10.1021/ol901963v

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


  14 in total

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

Authors:  D Magdziak; S J Meek; T R R Pettus
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2.  Synthetic Studies towards Maoecrystal V.

Authors:  Feng Peng; Maolin Yu; Samuel J Danishefsky
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3.  An expedient asymmetric synthesis of platencin.

Authors:  K C Nicolaou; Qiao-Yan Toh; David Y-K Chen
Journal:  J Am Chem Soc       Date:  2008-07-30       Impact factor: 15.419

Review 4.  The Diels--Alder reaction in total synthesis.

Authors:  K C Nicolaou; Scott A Snyder; Tamsyn Montagnon; Georgios Vassilikogiannakis
Journal:  Angew Chem Int Ed Engl       Date:  2002-05-17       Impact factor: 15.336

5.  Synthetic study toward the total synthesis of maoecrystal V.

Authors:  Jianxian Gong; Guang Lin; Chuang-chuang Li; Zhen Yang
Journal:  Org Lett       Date:  2009-11-05       Impact factor: 6.005

6.  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

7.  Maoecrystal V, cytotoxic diterpenoid with a novel C19 skeleton from Isodon eriocalyx (Dunn.) hara.

Authors:  Sheng-Hong Li; Jia Wang; Xue-Mei Niu; Yun-Heng Shen; Hong-Jie Zhang; Han-Dong Sun; Ma-Lin Li; Qin-E Tian; Yang Lu; Peng Cao; Qi-Tai Zheng
Journal:  Org Lett       Date:  2004-11-11       Impact factor: 6.005

8.  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

9.  Explorations into neolignan biosynthesis: concise total syntheses of helicterin B, helisorin, and helisterculin A from a common intermediate.

Authors:  Scott A Snyder; Ferenc Kontes
Journal:  J Am Chem Soc       Date:  2009-02-11       Impact factor: 15.419

10.  Efficient synthesis and subsequent transformations of phenylsulfanylbicyclo[2.2.2]octenones and phenylselenylbicyclo[2.2.2]octenones.

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  13 in total

1.  Studies toward the synthesis of maoecrystal V.

Authors:  Zhenhua Gu; Armen Zakarian
Journal:  Org Lett       Date:  2011-01-27       Impact factor: 6.005

2.  Toward the total synthesis of maoecrystal V: an intramolecular Diels-Alder route to the maoecrystal V pentacyclic core with the appropriate relative stereochemistry.

Authors:  Feng Peng; Samuel J Danishefsky
Journal:  Tetrahedron Lett       Date:  2011-04-27       Impact factor: 2.415

3.  The Synthesis and Antimicrobial Activity of Heterocyclic Derivatives of Totarol.

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Journal:  ACS Med Chem Lett       Date:  2012-08-28       Impact factor: 4.345

4.  A synthesis of the carbocyclic core of maoecrystal V.

Authors:  Kiel E Lazarski; Dennis X Hu; Charlotte L Stern; Regan J Thomson
Journal:  Org Lett       Date:  2010-07-02       Impact factor: 6.005

5.  Directed oxidative cyclizations to C2- or C4-positions of indole: efficient construction of the bicyclo[4.3.1]decane core of welwitindolinones.

Authors:  Vikram Bhat; James A Mackay; Viresh H Rawal
Journal:  Org Lett       Date:  2011-05-26       Impact factor: 6.005

6.  Total synthesis of N-methylwelwitindolinone D isonitrile.

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Journal:  J Am Chem Soc       Date:  2011-03-29       Impact factor: 15.419

7.  Total synthesis of maoecrystal V: early-stage C-H functionalization and lactone assembly by radical cyclization.

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Journal:  J Am Chem Soc       Date:  2013-09-23       Impact factor: 15.419

8.  Evaluation of 'east-to-west' ether-forming strategies for the total synthesis of maoecrystal V.

Authors:  Kiel E Lazarski; Berkcan Akpinar; Regan J Thomson
Journal:  Tetrahedron Lett       Date:  2013-02-13       Impact factor: 2.415

9.  Oxidative Coupling of Enolates, Enol Silanes and Enamines: Methods and Natural Product Synthesis.

Authors:  Fenghai Guo; Michael D Clift; Regan J Thomson
Journal:  European J Org Chem       Date:  2012-07-16

10.  Total synthesis of (±)-maoecrystal V.

Authors:  Feng Peng; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2012-11-05       Impact factor: 15.419
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