Literature DB >> 11735588

A stereoselective synthesis of the C10-C31 (BCDEF ring) portion of pinnatoxin A.

S Nakamura1, J Inagaki, T Sugimoto, M Kudo, M Nakajima, S Hashimoto.   

Abstract

[reaction: see text] An efficient synthesis of the C10-C31 (BCDEF ring) portion of pinnatoxin A has been achieved. The key step is a highly stereoselective construction of the dispiroketal (BCD ring) system employing an intramolecular hetero-Michael reaction of a reversibly formed hemiketal alkoxide through the use of LiOMe.

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Year:  2001        PMID： 11735588     DOI： 10.1021/ol0168364

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


  4 in total

1.  Unified total synthesis of pteriatoxins and their diastereomers.

Authors:  Fumiyoshi Matsuura; René Peters; Masahiro Anada; Scott S Harried; Junliang Hao; Yoshito Kishi
Journal:  J Am Chem Soc       Date:  2006-06-14       Impact factor: 15.419

2.  Amphidinolide B: total synthesis, structural investigation, and biological evaluation.

Authors:  Liang Lu; Wei Zhang; Sangkil Nam; David A Horne; Richard Jove; Rich G Carter
Journal:  J Org Chem       Date:  2013-02-13       Impact factor: 4.354

3.  Total synthesis and stereochemistry of pinnatoxins B and C.

Authors:  Fumiyoshi Matsuura; Junliang Hao; Reinhard Reents; Yoshito Kishi
Journal:  Org Lett       Date:  2006-07-20       Impact factor: 6.005

4.  Total synthesis of pinnatoxins A and G and revision of the mode of action of pinnatoxin A.

Authors:  Romulo Araoz; Denis Servent; Jordi Molgó; Bogdan I Iorga; Carole Fruchart-Gaillard; Evelyne Benoit; Zhenhua Gu; Craig Stivala; Armen Zakarian
Journal:  J Am Chem Soc       Date:  2011-06-17       Impact factor: 15.419
  4 in total

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