Literature DB >> 10956507

Asymmetric synthesis of (-)-tetrahydrolipstatin: an anti-aldol-based strategy.

A K Ghosh1, S Fidanze.   

Abstract

A stereoselective synthesis of (-)-tetrahydrolipstatin is described. The synthesis involves an asymmetric ester derived titanium enolate anti-aldol reaction, a nitro-aldol reaction to append the C-2' C(11) side chain, and a diastereoselective reduction of a beta-hydroxy ketone to an anti-1,3-diol functionality followed by its elaboration to (-)-tetrahydrolipstatin.

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Year:  2000        PMID： 10956507     DOI： 10.1021/ol000070a

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


  9 in total

1.  A Stereoselective Anti-Aldol Route to (3R,3aS,6aR)-Hexahydrofuro[2,3-b] furan-3-ol: A Key Ligand for a New Generation of HIV Protease Inhibitors.

Authors:  Arun K Ghosh; Jianfeng Li; Ramu Sridhar Perali
Journal:  Synthesis (Stuttg)       Date:  2006-09       Impact factor: 3.157

2.  Chelation-controlled ester-derived titanium enolate aldol reaction: diastereoselective syn-aldols with mono- and bidentate aldehydes.

Authors:  Arun K Ghosh; Jae-Hun Kim
Journal:  Tetrahedron Lett       Date:  2002-07-17       Impact factor: 2.415

3.  Synthesis of Bioactive Natural Products by Asymmetric syn- and anti-Aldol Reactions.

Authors:  Arun K Ghosh; Zachary L Dawson
Journal:  Synthesis (Stuttg)       Date:  2009-09       Impact factor: 3.157

4.  A concise, phosphate-mediated approach to the total synthesis of (-)-tetrahydrolipstatin.

Authors:  Phanindra K M Venukadasula; Rambabu Chegondi; Soma Maitra; Paul R Hanson
Journal:  Org Lett       Date:  2010-04-02       Impact factor: 6.005

5.  Capturing the essence of organic synthesis: from bioactive natural products to designed molecules in today's medicine.

Authors:  Arun K Ghosh
Journal:  J Org Chem       Date:  2010-10-11       Impact factor: 4.354

6.  Stereochemical Structure Activity Relationship Studies (S-SAR) of Tetrahydrolipstatin.

Authors:  Xiaofan Liu; Yanping Wang; Richard I Duclos; George A O'Doherty
Journal:  ACS Med Chem Lett       Date:  2018-02-21       Impact factor: 4.345

Review 7.  Harnessing nature's insight: design of aspartyl protease inhibitors from treatment of drug-resistant HIV to Alzheimer's disease.

Authors:  Arun K Ghosh
Journal:  J Med Chem       Date:  2009-04-23       Impact factor: 7.446

8.  Asymmetric synthesis of anti-aldol segments via a nonaldol route: synthetic applications to statines and (-)-tetrahydrolipstatin.

Authors:  Arun K Ghosh; Khriesto Shurrush; Sarang Kulkarni
Journal:  J Org Chem       Date:  2009-06-19       Impact factor: 4.354

9.  Total synthesis of tetrahydrolipstatin and stereoisomers via a highly regio- and diastereoselective carbonylation of epoxyhomoallylic alcohols.

Authors:  Michael Mulzer; Brandon J Tiegs; Yanping Wang; Geoffrey W Coates; George A O'Doherty
Journal:  J Am Chem Soc       Date:  2014-07-18       Impact factor: 15.419
  9 in total

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