Literature DB >> 11525658

Synthesis and absolute stereochemistry of roseophilin.

P E Harrington1, M A Tius.   

Abstract

The enantiospecific total synthesis of natural roseophilin has been completed in 7.0% overall yield over 15 steps by means of an asymmetric cyclopentannelation. This establishes the absolute configuration of the natural product as 22R,23R. Cyclopentenone (+)-12 was prepared in 78% yield and 86% ee in the key step.

Entities:  

Mesh:

Substances:

Year:  2001        PMID: 11525658     DOI: 10.1021/ja011242h

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  16 in total

1.  Discovering New Reactions with N-Heterocyclic Carbene Catalysis.

Authors:  Eric M Phillips; Audrey Chan; Karl A Scheidt
Journal:  Aldrichimica Acta       Date:  2009       Impact factor: 3.667

2.  Neutral Nazarov-type cyclization catalyzed by palladium(0).

Authors:  Naoyuki Shimada; Craig Stewart; William F Bow; Anais Jolit; Kahoano Wong; Zhe Zhou; Marcus A Tius
Journal:  Angew Chem Int Ed Engl       Date:  2012-04-26       Impact factor: 15.336

Review 3.  Carbene catalysts.

Authors:  Jennifer L Moore; Tomislav Rovis
Journal:  Top Curr Chem       Date:  2010

4.  Design of chiral auxiliaries for the allene ether nazarov cyclization.

Authors:  April R Banaag; Marcus A Tius
Journal:  J Am Chem Soc       Date:  2007-04-11       Impact factor: 15.419

5.  Formal synthesis of (+/-)-roseophilin.

Authors:  Abdallah Y Bitar; Alison J Frontier
Journal:  Org Lett       Date:  2009-01-01       Impact factor: 6.005

6.  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

7.  The Catalytic Asymmetric Intramolecular Stetter Reaction.

Authors:  Javier Read de Alaniz; Tomislav Rovis
Journal:  Synlett       Date:  2009-05       Impact factor: 2.454

8.  Asymmetric Nazarov Cyclizations.

Authors:  Naoyuki Shimada; Craig Stewart; Marcus A Tius
Journal:  Tetrahedron       Date:  2011-08-19       Impact factor: 2.457

9.  Modular access to complex prodiginines: total synthesis of (+)-roseophilin via its 2-azafulvene prototropisomer.

Authors:  James H Frederich; Patrick G Harran
Journal:  J Am Chem Soc       Date:  2013-03-01       Impact factor: 15.419

Review 10.  A continuum of progress: applications of N-hetereocyclic carbene catalysis in total synthesis.

Authors:  Javier Izquierdo; Gerri E Hutson; Daniel T Cohen; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2012-10-16       Impact factor: 15.336

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.