Literature DB >> 19354245

Total synthesis of the sphingolipid biosynthesis inhibitor fumonisin B(1).

Claney L Pereira1, Yi-Hung Chen, Frank E McDonald.   

Abstract

The first total synthesis of the sphingolipid biosynthesis inhibitor fumonisin B(1) has been achieved. This convergent synthesis utilizes oxonia Cope rearrangements to prepare two key homoallylic alcohols, which are then functionalized to the primary components A and B for cross-coupling. Other highlights of our approach include a new and efficient synthesis of the diprotected tricarballylic acid C and a global deprotection strategy as the final step.

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Year:  2009        PMID: 19354245     DOI: 10.1021/ja9009265

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


  5 in total

Review 1.  Toward a symphony of reactivity: cascades involving catalysis and sigmatropic rearrangements.

Authors:  Amanda C Jones; Jeremy A May; Richmond Sarpong; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2014-03-03       Impact factor: 15.336

2.  Rh2(II)-Catalyzed Intermolecular N-Aryl Aziridination of Olefins Using Nonactivated N Atom Precursors.

Authors:  Tianning Deng; Wrickban Mazumdar; Yuki Yoshinaga; Pooja B Patel; Dana Malo; Tala Malo; Donald J Wink; Tom G Driver
Journal:  J Am Chem Soc       Date:  2021-11-08       Impact factor: 15.419

3.  Enantio- and diastereoselective synthesis of syn-β-hydroxy-α-vinyl carboxylic esters via reductive aldol reactions of ethyl allenecarboxylate with 10-TMS-9-Borabicyclo[3.3.2]decane and DFT analysis of the hydroboration pathway.

Authors:  Jeremy Kister; Daniel H Ess; William R Roush
Journal:  Org Lett       Date:  2013-10-18       Impact factor: 6.005

Review 4.  Fumonisins: Impact on Agriculture, Food, and Human Health and their Management Strategies.

Authors:  Madhu Kamle; Dipendra K Mahato; Sheetal Devi; Kyung Eun Lee; Sang G Kang; Pradeep Kumar
Journal:  Toxins (Basel)       Date:  2019-06-07       Impact factor: 4.546

Review 5.  Application of cyclic phosphonamide reagents in the total synthesis of natural products and biologically active molecules.

Authors:  Thilo Focken; Stephen Hanessian
Journal:  Beilstein J Org Chem       Date:  2014-08-13       Impact factor: 2.883

  5 in total

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