Literature DB >> 17944481

Synthesis of (-)-chaetominine.

Barry B Snider1, Xiaoxing Wu.   

Abstract

The tricyclic hydroxy imidazolidinone was converted to chaetominine in seven steps in 22% overall yield. The key step was the construction of the delta-lactam by heating an amino ester with a catalytic amount of DMAP in toluene at reflux.

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Year:  2007        PMID： 17944481      PMCID： PMC2527753          DOI： 10.1021/ol7022483

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


  5 in total

1.  A concise stereoselective route to the indoline spiroaminal framework of neoxaline and oxaline.

Authors:  Toshiaki Sunazuka; Tatsuya Shirahata; Satoshi Tsuchiya; Tomoyasu Hirose; Ryuma Mori; Yoshihiro Harigaya; Isao Kuwajima; Satoshi Omura
Journal:  Org Lett       Date:  2005-03-03       Impact factor: 6.005

2.  Chaetominine, a cytotoxic alkaloid produced by endophytic Chaetomium sp. IFB-E015.

Authors:  Rui H Jiao; Shu Xu; Jun Y Liu; Hui M Ge; Hui Ding; Chen Xu; Hai L Zhu; Ren X Tan
Journal:  Org Lett       Date:  2006-12-07       Impact factor: 6.005

3.  Discovery through total synthesis: a retrospective on the himastatin problem.

Authors:  T M Kamenecka; S J Danishefsky
Journal:  Chemistry       Date:  2001-01-05       Impact factor: 5.236

4.  Total synthesis of (-)-fumiquinazolines A, B, C, E, H, and I. Approaches to the synthesis of fiscalin A.

Authors:  Barry B Snider; Hongbo Zeng
Journal:  J Org Chem       Date:  2003-01-24       Impact factor: 4.354

5.  Determination of the absolute configurations of flexible molecules: synthesis and theoretical simulation of electronic circular dichroism/optical rotation of some pyrrolo[2,3-b]indoline alkaloids--a case study.

Authors:  Egidio Giorgio; Katsunori Tanaka; Luisella Verotta; Koji Nakanishi; Nina Berova; Carlo Rosini
Journal:  Chirality       Date:  2007-06       Impact factor: 2.437
  5 in total
  2 in total

1.  Scalable total syntheses of N-linked tryptamine dimers by direct indole-aniline coupling: psychotrimine and kapakahines B and F.

Authors:  Timothy Newhouse; Chad A Lewis; Kyle J Eastman; Phil S Baran
Journal:  J Am Chem Soc       Date:  2010-05-26       Impact factor: 15.419

2.  Photoassisted synthesis of enantiopure alkaloid mimics possessing unprecedented polyheterocyclic cores.

Authors:  N N Bhuvan Kumar; Olga A Mukhina; Andrei G Kutateladze
Journal:  J Am Chem Soc       Date:  2013-06-21       Impact factor: 15.419
  2 in total

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