Literature DB >> 11506625

Stereoselective syntheses of the C'D'E'F'-ring system of maitotoxin and the FG-ring system of gambierol.

Y Sakamoto1, G Matsuo, H Matsukura, T Nakata.   

Abstract

[structure: see text]. The stereoselective syntheses of the C'D'E'F'-ring system of maitotoxin and the FG-ring system of gambierol were accomplished. The key steps involve 6-endo-cyclization of methylepoxide, SmI2-induced reductive cyclization, 6-endo-cyclization of vinylepoxide, and formation of the lactone ring.

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Year:  2001        PMID: 11506625     DOI: 10.1021/ol016355k

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


  7 in total

Review 1.  The continuing saga of the marine polyether biotoxins.

Authors:  K C Nicolaou; Michael O Frederick; Robert J Aversa
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

2.  Maitotoxin: An Inspiration for Synthesis.

Authors:  K C Nicolaou; Robert J Aversa
Journal:  Isr J Chem       Date:  2011-04       Impact factor: 3.333

3.  Synthesis of the C'D'E'F' domain of maitotoxin.

Authors:  K C Nicolaou; Jae Hong Seo; Tsuyoshi Nakamura; Robert J Aversa
Journal:  J Am Chem Soc       Date:  2010-12-17       Impact factor: 15.419

4.  Synthesis of the ABCDEFG ring system of maitotoxin.

Authors:  K C Nicolaou; Robert J Aversa; Jian Jin; Fatima Rivas
Journal:  J Am Chem Soc       Date:  2010-05-19       Impact factor: 15.419

5.  Surveying approaches to the formation of carbon-carbon bonds between a pyran and an adjacent ring.

Authors:  Jeffrey D Frein; Tomislav Rovis
Journal:  Tetrahedron       Date:  2006-05-01       Impact factor: 2.457

6.  Synthesis and biological evaluation of QRSTUVWXYZA' domains of maitotoxin.

Authors:  K C Nicolaou; Philipp Heretsch; Tsuyoshi Nakamura; Anna Rudo; Michio Murata; Keiichi Konoki
Journal:  J Am Chem Soc       Date:  2014-11-06       Impact factor: 15.419

Review 7.  Synthetic and biosynthetic methods for selective cyclisations of 4,5-epoxy alcohols to tetrahydropyrans.

Authors:  James I Bowen; Luoyi Wang; Matthew P Crump; Christine L Willis
Journal:  Org Biomol Chem       Date:  2022-02-09       Impact factor: 3.876

  7 in total

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