Literature DB >> 26760683

A Pot-Economical Approach to the Total Synthesis of Sch-725674.

Mahipal Bodugam1, Salim Javed1, Arghya Ganguly1, Jessica Torres1, Paul R Hanson1.   

Abstract

A pot-economical total synthesis of antifungal Sch-725674, 1, is reported. The approach takes advantage of a number of one-pot, sequential transformations, including a phosphate tether-mediated one-pot, sequential RCM/CM/chemoselective hydrogenation protocol, a one-pot tosylation/acrylation sequence, and a one-pot, sequential Finkelstein reaction/Boord olefination/acetonide deprotection procedure to streamline the synthesis route by reducing isolation and purification procedures, thus saving time. Overall, an asymmetric route has been developed that is efficiently accomplished in seven pots from phosphate (S,S)-triene and with minimal purification.

Entities:  

Mesh：

Substances：

Year:  2016        PMID： 26760683      PMCID： PMC4852165          DOI： 10.1021/acs.orglett.5b03547

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


  28 in total

1.  Structure elucidation of Sch 725674 from Aspergillus sp.

Authors:  Shu-Wei Yang; Tze-Ming Chan; Joseph Terracciano; David Loebenberg; Mahesh Patel; Min Chu
Journal:  J Antibiot (Tokyo)       Date:  2005-08       Impact factor: 2.649

2.  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 3.  One-pot quadruple/triple reaction sequence: a useful tool for the synthesis of natural products.

Authors:  K Kashinath; D Srinivasa Reddy
Journal:  Org Biomol Chem       Date:  2014-11-14       Impact factor: 3.876

4.  Pot economy in the synthesis of prostaglandin A1 and E1 methyl esters.

Authors:  Yujiro Hayashi; Shigenobu Umemiya
Journal:  Angew Chem Int Ed Engl       Date:  2013-02-13       Impact factor: 15.336

5.  Multivalent activation in temporary phosphate tethers: a new tether for small molecule synthesis.

Authors:  Alan Whitehead; Matthew D McReynolds; Joel D Moore; Paul R Hanson
Journal:  Org Lett       Date:  2005-07-21       Impact factor: 6.005

6.  Enantioselective synthesis of 2-deoxy- and 2,3-dideoxyhexoses.

Authors:  Michael H Haukaas; George A O'Doherty
Journal:  Org Lett       Date:  2002-05-16       Impact factor: 6.005

7.  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

Review 8.  Function-oriented synthesis, step economy, and drug design.

Authors:  Paul A Wender; Vishal A Verma; Thomas J Paxton; Thomas H Pillow
Journal:  Acc Chem Res       Date:  2007-12-27       Impact factor: 22.384

9.  An efficient, modular approach for the synthesis of (+)-strictifolione and a related natural product.

Authors:  Susanthi Jayasinghe; Phanindra K M Venukadasula; Paul R Hanson
Journal:  Org Lett       Date:  2013-12-02       Impact factor: 6.005

10.  Enantiospecific total synthesis of macrolactone Sch 725674.

Authors:  Amit K Bali; Sunil K Sunnam; Kavirayani R Prasad
Journal:  Org Lett       Date:  2014-07-17       Impact factor: 6.005
View more
  5 in total

1.  Modular Synthesis of Novel Macrocycles Bearing α,β-Unsaturated Chemotypes through a Series of One-Pot, Sequential Protocols.

Authors:  Salim Javed; Mahipal Bodugam; Jessica Torres; Arghya Ganguly; Paul R Hanson
Journal:  Chemistry       Date:  2016-04-05       Impact factor: 5.236

2.  P-Tether-Mediated, Iterative SN2'-Cuprate Alkylation Strategy to Skipped Polyol Stereotetrads: Utility of an Oxidative "Function Switch" with Phosphite-Borane Tethers.

Authors:  Jana L Markley; Paul R Hanson
Journal:  Org Lett       Date:  2017-05-04       Impact factor: 6.005

3.  P-Stereogenic Bicyclo[4.3.1]phosphite Boranes: Synthesis and Utility of Tunable P-Tether Systems for the Desymmetrization of C2-Symmetric 1,3-anti-Diols.

Authors:  Jana L Markley; Paul R Hanson
Journal:  Org Lett       Date:  2017-05-04       Impact factor: 6.005

4.  Synthesis of the C9-C25 Subunit of Spirastrellolide B.

Authors:  Soma Maitra; Mahipal Bodugam; Salim Javed; Paul R Hanson
Journal:  Org Lett       Date:  2016-06-14       Impact factor: 6.005

5.  Regio- and Stereoselective Homologation of 1,2-Bis(Boronic Esters): Stereocontrolled Synthesis of 1,3-Diols and Sch 725674.

Authors:  Alexander Fawcett; Dominik Nitsch; Muhammad Ali; Joseph M Bateman; Eddie L Myers; Varinder K Aggarwal
Journal:  Angew Chem Int Ed Engl       Date:  2016-10-26       Impact factor: 15.336
  5 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.