Literature DB >> 15968358

A total synthesis of (+/-)-alpha-cyclopiazonic acid using a cationic cascade.

Charlotte M Haskins1, David W Knight.   

Abstract

The indolic terpene alkaloid alpha-cyclopiazonic acid has been prepared in 11 steps from indole-4-methanol; the key step is a carbocationic cascade, terminated by a 4-nitrosulfonamide group and initiated by benzylic carbocation formation directly from the intermediate , which gives the tetracyclic product in 74% yield.

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Year:  2005        PMID: 15968358     DOI: 10.1039/b417625c

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  3 in total

1.  Catalytic Alkene Cyclization Reactions for the Stereoselective Synthesis of Complex "Terpenoid-like" Heterocycles.

Authors:  Jared T Moore; Cristian Soldi; James C Fettinger; Jared T Shaw
Journal:  Chem Sci       Date:  2012-10-25       Impact factor: 9.825

2.  An efficient synthesis of tetramic acid derivatives with extended conjugation from L-ascorbic acid.

Authors:  Biswajit K Singh; Surendra S Bisht; Rama P Tripathi
Journal:  Beilstein J Org Chem       Date:  2006-12-06       Impact factor: 2.883

3.  Enantioselective Synthesis of the Cyclopiazonic Acid Family Using Sulfur Ylides.

Authors:  Oleksandr Zhurakovskyi; Yunus E Türkmen; Lorenz E Löffler; Vijayalakshmi A Moorthie; C Chun Chen; Michael A Shaw; Mark R Crimmin; Marco Ferrara; Mushtaq Ahmad; Mehrnoosh Ostovar; Johnathan V Matlock; Varinder K Aggarwal
Journal:  Angew Chem Int Ed Engl       Date:  2018-01-09       Impact factor: 15.336

  3 in total

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