Literature DB >> 14510553

Synthesis of (-)-tetrodotoxin: preparation of an advanced cyclohexenone intermediate.

Douglass F Taber1, Pierre H Storck.   

Abstract

The preparation of an advanced intermediate toward the enantioselective synthesis of tetrodotoxin is outlined. The enantiomerically pure cyclopentene 15 was generated from ketone 14 by alkylidene carbene insertion with retention of absolute configuration. An ozonolysis/aldol sequence first produced the trans cyclohexenone, which upon epimerization gave the more stable cis enone 18.

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Year:  2003        PMID： 14510553     DOI： 10.1021/jo0301189

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  3 in total

1.  A model study toward the total synthesis of N-deacetyllappaconitine.

Authors:  Douglass F Taber; Jiang-Lin Liang; Bei Chen; Lisi Cai
Journal:  J Org Chem       Date:  2005-10-28       Impact factor: 4.354

2.  Structure-activity relationships of antitubercular nitroimidazoles. 2. Determinants of aerobic activity and quantitative structure-activity relationships.

Authors:  Pilho Kim; Sunhee Kang; Helena I Boshoff; Jan Jiricek; Margaret Collins; Ramandeep Singh; Ujjini H Manjunatha; Pornwaratt Niyomrattanakit; Liang Zhang; Michael Goodwin; Thomas Dick; Thomas H Keller; Cynthia S Dowd; Clifton E Barry
Journal:  J Med Chem       Date:  2009-03-12       Impact factor: 7.446

Review 3.  The chemical synthesis of tetrodoxin: an ongoing quest.

Authors:  Jaclyn Chau; Marco A Ciufolini
Journal:  Mar Drugs       Date:  2011-10-20       Impact factor: 6.085
  3 in total

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