Literature DB >> 17630803

Total synthesis of (+/-)-terpestacin and (+/-)-11-epi-terpestacin.

Gideon O Berger1, Marcus A Tius.   

Abstract

The total synthesis of racemic terpestacin and 11-epi-terpestacin using the allene ether Nazarov reaction as the key step is described. All stereochemistry is derived from the stereogenic carbon atom that is formed during the Nazarov reaction.

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Year:  2007        PMID： 17630803     DOI： 10.1021/jo070923d

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  8 in total

1.  A highly reactive dicationic iridium(III) catalyst for the polarized Nazarov cyclization reaction.

Authors:  Tulaza Vaidya; Abdurrahman C Atesin; Ildiko R Herrick; Alison J Frontier; Richard Eisenberg
Journal:  Angew Chem Int Ed Engl       Date:  2010-04-26       Impact factor: 15.336

2.  Traceless chiral auxiliaries for the allene ether Nazarov cyclization.

Authors:  April R Banaag; Marcus A Tius
Journal:  J Org Chem       Date:  2008-09-23       Impact factor: 4.354

3.  Metallacycle-Mediated Cross-Coupling in Natural Product Synthesis.

Authors:  Natasha F O'Rourke; Matthew J Kier; Glenn C Micalizio
Journal:  Tetrahedron       Date:  2016-09-07       Impact factor: 2.457

4.  Cyclic 1,2-diketones as core building blocks: a strategy for the total synthesis of (-)-terpestacin.

Authors:  Barry M Trost; Guangbin Dong; Jennifer A Vance
Journal:  Chemistry       Date:  2010-06-01       Impact factor: 5.236

5.  Beyond the Divinyl Ketone: Innovations in the Generation and Nazarov Cyclization of Pentadienyl Cation Intermediates.

Authors:  William T Spencer; Tulaza Vaidya; Alison J Frontier
Journal:  European J Org Chem       Date:  2013-06-01

6.  Interrupting the Nazarov cyclization with indoles.

Authors:  Ashok K Basak; Marcus A Tius
Journal:  Org Lett       Date:  2008-08-23       Impact factor: 6.005

7.  Mixed aggregates of 1-methoxyallenyllithium with lithium chloride.

Authors:  Lawrence M Pratt; Darryl D Dixon; Marcus A Tius
Journal:  ChemistryOpen       Date:  2014-11-19       Impact factor: 2.911

8.  Salen promoted enantioselective Nazarov cyclizations of activated and unactivated dienones.

Authors:  Gerri E Hutson; Yunus E Türkmen; Viresh H Rawal
Journal:  J Am Chem Soc       Date:  2013-03-25       Impact factor: 15.419
  8 in total

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