Literature DB >> 18855401

Concise enantioselective total synthesis of neopeltolide macrolactone highlighted by ether transfer.

Rendy Kartika1, Thomas R Gruffi, Richard E Taylor.   

Abstract

A concise total synthesis of neopeltolide macrolactone has been accomplished in 14 steps in the longest linear sequence, 15 steps overall from commercially available materials. The present synthesis was highlighted by successful exploitation of ether transfer methodology and a radical cyclization reaction to directly establish the requisite stereochemistry of the tetrahydropyran core.

Entities:  

Mesh:

Substances:

Year:  2008        PMID: 18855401     DOI: 10.1021/ol802254z

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


  19 in total

1.  Toward an enantioselective synthesis of (-)-zampanolide: preparation of the C9-C20 region.

Authors:  Matthew R Wilson; Richard E Taylor
Journal:  Org Lett       Date:  2012-06-21       Impact factor: 6.005

2.  Enantioselective total synthesis of macrolide (+)-neopeltolide.

Authors:  Arun K Ghosh; Khriesto A Shurrush; Zachary L Dawson
Journal:  Org Biomol Chem       Date:  2013-10-11       Impact factor: 3.876

3.  Concise enantioselective synthesis of diospongins A and B.

Authors:  Eric Stefan; Ansel P Nalin; Richard E Taylor
Journal:  Tetrahedron       Date:  2013-09-09       Impact factor: 2.457

4.  Total Synthesis and Structural Reassignment of Lyngbyaloside C Highlighted by Intermolecular Ketene Esterification.

Authors:  Chia-Fu Chang; Eric Stefan; Richard E Taylor
Journal:  Chemistry       Date:  2015-06-23       Impact factor: 5.236

5.  Total synthesis and structure-activity investigation of the marine natural product neopeltolide.

Authors:  Daniel W Custar; Thomas P Zabawa; John Hines; Craig M Crews; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2009-09-02       Impact factor: 15.419

Review 6.  Thiazole and oxazole alkaloids: isolation and synthesis.

Authors:  Danilo Davyt; Gloria Serra
Journal:  Mar Drugs       Date:  2010-11-05       Impact factor: 5.118

7.  Polyol synthesis with beta-oxyanionic alkyllithium reagents: syntheses of aculeatins A, B, and D.

Authors:  Viengkham Malathong; Scott D Rychnovsky
Journal:  Org Lett       Date:  2009-09-17       Impact factor: 6.005

8.  Oxidative carbocation formation in macrocycles: synthesis of the neopeltolide macrocycle.

Authors:  Wangyang Tu; Paul E Floreancig
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

9.  Strategies and Methods for the Synthesis of Anticancer Natural Product Neopeltolide and its Analogs.

Authors:  Yu Bai; Mingji Dai
Journal:  Curr Org Chem       Date:  2015       Impact factor: 2.180

10.  Total synthesis of brevisamide.

Authors:  Olugbeminiyi O Fadeyi; Craig W Lindsley
Journal:  Org Lett       Date:  2009-09-03       Impact factor: 6.005

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.