Literature DB >> 20305722

Enantioselective syntheses of candenatenins B and C using a chiral anthracene auxiliary.

Amanda L Jones1, Xiang Liu, John K Snyder.   

Abstract

An asymmetric synthesis of two anticancer natural products, candenatenins B and C, is described, leading to a revision of the originally assigned stereochemistry. The synthesis follows a Diels-Alder/retro-Diels Alder strategy using a chiral anthracene auxiliary to access both targets with 90% ee. The inherent structural qualities of the auxiliary allow for both regio- and diastereoselective transformations.

Entities:  

Year:  2010        PMID: 20305722      PMCID: PMC2839163          DOI: 10.1016/j.tetlet.2009.12.108

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN: 0040-4039            Impact factor:   2.415


  15 in total

1.  The concept of transient chirality in the stereoselective synthesis of functionalized cycloalkenes applying the retro-diels-alder methodology.

Authors:  A J Klunder; J Zhu; B Zwanenburg
Journal:  Chem Rev       Date:  1999-05-12       Impact factor: 60.622

2.  Stereoselective diels-alder reactions of chiral anthracenes

Authors: 
Journal:  Org Lett       Date:  2000-08-10       Impact factor: 6.005

3.  New cyclohexadienone derivatives: preparation and chiral discrimination in high-pressure Diels-Alder cycloadditions.

Authors:  M E Trân-Huu-Dâu; R Wartchow; E Winterfeldt; Y S Wong
Journal:  Chemistry       Date:  2001-06-01       Impact factor: 5.236

4.  Chiral anthracene and anthrone templates as stereocontrolling elements in Diels-Alder/retro Diels-Alder sequences.

Authors:  Kerrie L Burgess; Matthew S Corbett; Paul Eugenio; Neil J Lajkiewicz; Xiang Liu; Amitav Sanyal; Wanlin Yan; Qian Yuan; John K Snyder
Journal:  Bioorg Med Chem       Date:  2005-09-01       Impact factor: 3.641

5.  Highly diastereoselective Diels-Alder cycloadditions of 9R-(1-methoxyethyl)anthracene with p-benzoquinone.

Authors:  Harry Adams; Simon Jones; Isaac Ojea-Jimenez
Journal:  Org Biomol Chem       Date:  2006-05-08       Impact factor: 3.876

6.  Candenatenins A-F, phenolic compounds from the heartwood of Dalbergia candenatensis.

Authors:  Sarot Cheenpracha; Chatchanok Karalai; Chanita Ponglimanont; Akkharawit Kanjana-Opas
Journal:  J Nat Prod       Date:  2009-08       Impact factor: 4.050

7.  A new chiral anthracene for the asymmetric Diels-Alder/retro-Diels-Alder sequence.

Authors:  Kerrie L Burgess; Neil J Lajkiewicz; Amitav Sanyal; Wanlin Yan; John K Snyder
Journal:  Org Lett       Date:  2005-01-06       Impact factor: 6.005

8.  Understanding the stereoselection induced by chiral anthracene templates in Diels-Alder cycloaddition: a DFT study.

Authors:  Nihan Celebi-Olçüm; Amitav Sanyal; Viktorya Aviyente
Journal:  J Org Chem       Date:  2009-03-20       Impact factor: 4.354

9.  Syntheses of highly substituted enantiopure C6 and C7 enones(1).

Authors:  Jerry Evarts; Eduardo Torres; Philip L Fuchs
Journal:  J Am Chem Soc       Date:  2002-09-18       Impact factor: 15.419

10.  Anthracene cycloadducts as highly selective chiral auxiliaries.

Authors:  Xiang Liu; John K Snyder
Journal:  J Org Chem       Date:  2008-03-06       Impact factor: 4.354

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