Literature DB >> 11950358

Stereocontrolled total synthesis of pancratistatin.

Sanghee Kim1, Hyojin Ko, Eunkyung Kim, Deukjoon Kim.   

Abstract

A new total synthesis of the antitumor alkaloids, pancratistatin (1), has been accomplished from readily available staring materials. The Claisen rearrangement of dihydropyranethylene 5 was employed to construct the A and C rings. Stereo- and regiocontrolled functional group interchange, such as iodolactonization, dihydroxylations, and a cyclic sulfate elimination reaction, allows for the production of the target natural product. [reaction: see text]

Entities:  

Mesh:

Substances:

Year:  2002        PMID: 11950358     DOI: 10.1021/ol0256419

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


  12 in total

Review 1.  Chemistry, biology, and medicinal potential of narciclasine and its congeners.

Authors:  Alexander Kornienko; Antonio Evidente
Journal:  Chem Rev       Date:  2008-05-20       Impact factor: 60.622

2.  Total Synthesis of (+)-Pancratistatin by the Rh(III)-Catalyzed Addition of a Densely Functionalized Benzamide to a Sugar-Derived Nitroalkene.

Authors:  Tyler J Potter; Jonathan A Ellman
Journal:  Org Lett       Date:  2017-05-24       Impact factor: 6.005

3.  Enantioselective Synthesis of Isocarbostyril Alkaloids and Analogs Using Catalytic Dearomative Functionalization of Benzene.

Authors:  Tanner W Bingham; Lucas W Hernandez; Daniel G Olson; Riley L Svec; Paul J Hergenrother; David Sarlah
Journal:  J Am Chem Soc       Date:  2018-12-20       Impact factor: 15.419

4.  TOTAL SYNTHESES OF PANCRATISTATIN. A REVIEW.

Authors:  Madhuri Manpadi; Alexander Kornienko
Journal:  Org Prep Proced Int       Date:  2009-02-18       Impact factor: 1.628

5.  An efficient synthesis of (+/-)-Lycoricidine featuring a Stille-IMDAF cycloaddition cascade.

Authors:  Hongjun Zhang; Albert Padwa
Journal:  Org Lett       Date:  2006-01-19       Impact factor: 6.005

6.  Synthesis of some members of the hydroxylated phenanthridone subclass of the Amaryllidaceae alkaloid family.

Authors:  Albert Padwa; Hongjun Zhang
Journal:  J Org Chem       Date:  2007-03-06       Impact factor: 4.354

7.  Catalytic asymmetric synthesis using feedstocks: an enantioselective route to 2-arylpropionic acids and 1-arylethyl amines via hydrovinylation of vinyl arenes.

Authors:  Craig R Smith; T V RajanBabu
Journal:  J Org Chem       Date:  2009-04-17       Impact factor: 4.354

8.  Synthesis of (+)-Pancratistatins via Catalytic Desymmetrization of Benzene.

Authors:  Lucas W Hernandez; Jola Pospech; Ulrich Klöckner; Tanner W Bingham; David Sarlah
Journal:  J Am Chem Soc       Date:  2017-10-25       Impact factor: 15.419

Review 9.  Discovery of natural product anticancer agents from biodiverse organisms.

Authors:  A Douglas Kinghorn; Young-Won Chin; Steven M Swanson
Journal:  Curr Opin Drug Discov Devel       Date:  2009-03

10.  A solution to the stereochemical problems posed by amaryllidaceae constituents using a highly syn-selective arylcuprate conjugate addition to γ-amino and γ-carbamato-α,β-enoates.

Authors:  Shiva K Rastogi; Alexander Kornienko
Journal:  Tetrahedron Asymmetry       Date:  2006-11-27
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.