Literature DB >> 15957948

A concise synthesis of (+)-SCH 351448.

Omid Soltani1, Jef K De Brabander.   

Abstract

[structure: see text] We describe a highly convergent synthetic approach to the natural product (+)-SCH 351448 (1)-a hexane-soluble heptacoordinate monosodium salt of a C(2)-symmetrical macrocyclic dilactone. Our approach implements a photochemical acylation as the key step to combine two nearly identical but orthogonal C1-C29 fragments, followed by a base-induced intramolecular acylation and deprotection to yield the natural product.

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Year:  2005        PMID: 15957948     DOI: 10.1021/ol0510769

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


  7 in total

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

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

2.  Assignment of absolute configuration to SCH 351448 via total synthesis.

Authors:  Lael L Cheung; Shinji Marumoto; Christopher D Anderson; Scott D Rychnovsky
Journal:  Org Lett       Date:  2008-06-11       Impact factor: 6.005

3.  Efficient asymmetric synthesis of (+)-SCH 351448.

Authors:  Sergei Bolshakov; James L Leighton
Journal:  Org Lett       Date:  2005-08-18       Impact factor: 6.005

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.  Phosphate tether-mediated approach to the formal total synthesis of (-)-salicylihalamides A and B.

Authors:  Rambabu Chegondi; Mary M L Tan; Paul R Hanson
Journal:  J Org Chem       Date:  2011-04-19       Impact factor: 4.354

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

Authors:  Gang Wang; Michael J Krische
Journal:  J Am Chem Soc       Date:  2016-06-23       Impact factor: 15.419

7.  A multifaceted phosphate tether: application to the C15-C30 subunit of dolabelides A-D.

Authors:  Alan Whitehead; Joshua D Waetzig; Christopher D Thomas; Paul R Hanson
Journal:  Org Lett       Date:  2008-03-07       Impact factor: 6.005

  7 in total

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