Literature DB >> 27337561

Total Synthesis of (+)-SCH 351448: Efficiency via Chemoselectivity and Redox-Economy Powered by Metal Catalysis.

Gang Wang1, Michael J Krische1.   

Abstract

The polyketide natural product (+)-SCH 351448, a macrodiolide ionophore bearing 14 stereogenic centers, is prepared in 14 steps (LLS). In eight prior syntheses, 22-32 steps were required. Multiple chemoselective and redox-economic functional group interconversions collectively contribute to a step-change in efficiency.

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Year:  2016        PMID： 27337561      PMCID： PMC4935581          DOI： 10.1021/jacs.6b04917

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


  42 in total

1.  Asymmetric transition-metal-catalyzed allylic alkylations: applications in total synthesis.

Authors:  Barry M Trost; Matthew L Crawley
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

2.  Total synthesis of (+)-SCH 351448.

Authors:  Kaicheng Zhu; James S Panek
Journal:  Org Lett       Date:  2011-08-11       Impact factor: 6.005

3.  Analysis of Past and Present Synthetic Methodologies on Medicinal Chemistry: Where Have All the New Reactions Gone?

Authors:  Dean G Brown; Jonas Boström
Journal:  J Med Chem       Date:  2015-12-01       Impact factor: 7.446

4.  A concise synthesis of (+)-SCH 351448.

Authors:  Omid Soltani; Jef K De Brabander
Journal:  Org Lett       Date:  2005-06-23       Impact factor: 6.005

5.  Enantioselective total synthesis of (+)-SCH 351448.

Authors:  Michael T Crimmins; Grace S Vanier
Journal:  Org Lett       Date:  2006-06-22       Impact factor: 6.005

6.  Redox economy in organic synthesis.

Authors:  Noah Z Burns; Phil S Baran; Reinhard W Hoffmann
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

Review 7.  The economies of synthesis.

Authors:  Timothy Newhouse; Phil S Baran; Reinhard W Hoffmann
Journal:  Chem Soc Rev       Date:  2009-08-21       Impact factor: 54.564

Review 8.  A receptor-mediated pathway for cholesterol homeostasis.

Authors:  M S Brown; J L Goldstein
Journal:  Science       Date:  1986-04-04       Impact factor: 47.728

9.  Prevention of undesirable isomerization during olefin metathesis.

Authors:  Soon Hyeok Hong; Daniel P Sanders; Choon Woo Lee; Robert H Grubbs
Journal:  J Am Chem Soc       Date:  2005-12-14       Impact factor: 15.419

10.  Total synthesis of (+)-SCH 351448.

Authors:  Eun Joo Kang; Eun Jin Cho; Young Eun Lee; Mi Kyung Ji; Dong Mok Shin; Young Keun Chung; Eun Lee
Journal:  J Am Chem Soc       Date:  2004-03-10       Impact factor: 15.419
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  3 in total

1.  Total Synthesis and Structural Validation of Phosdiecin A via Asymmetric Alcohol-Mediated Carbonyl Reductive Coupling.

Authors:  Franco Della-Felice; Ariel M Sarotti; Michael J Krische; Ronaldo A Pilli
Journal:  J Am Chem Soc       Date:  2019-08-21       Impact factor: 15.419

2.  Asymmetric synthesis of aryl/vinyl alkyl carbinol esters via Ni-catalyzed reductive arylation/vinylation of 1-chloro-1-alkanol esters.

Authors:  Deli Sun; Xianghua Tao; Guobin Ma; Jifen Wang; Yunrong Chen
Journal:  Chem Sci       Date:  2022-06-27       Impact factor: 9.969

3.  Expanding the antibacterial selectivity of polyether ionophore antibiotics through diversity-focused semisynthesis.

Authors:  Shaoquan Lin; Han Liu; Esben B Svenningsen; Malene Wollesen; Kristian M Jacobsen; Frederikke D Andersen; Jaime Moyano-Villameriel; Christine N Pedersen; Peter Nørby; Thomas Tørring; Thomas B Poulsen
Journal:  Nat Chem       Date:  2020-12-22       Impact factor: 24.427
  3 in total

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