Download PDF
Synthesis 2000; 2000(14): 2113-2116
DOI: 10.1055/s-2000-8711
special topic
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Synthetic Studies Toward caphalotaxine: Functionalization of Tertiary N-Acylhemiaminals by Nazarov Cyclization

Se-Ho Kim* , Jin Kun Cha
  • *Department of Chemistry, The University of Alabama, Tuscaloosa, AL 35487, USA; Fax +1(205)3 48 91 04; E-mail: jcha@bama.ua.edu
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

Functionalization of bicyclic N-acylhemiaminals, which are readily available by titanium-mediated intramolecular coupling of vinyl-tethered imides, has been achieved by use of the Nazarov cyclization to construct the carbon-carbon bond at the quaternary center. This synthetic strategy allows rapid entry to the key structural elements of cephalotaxine.

low-valent titanium - imide - N-acylhemiaminal - quaternary center - Nazarov cyclization

      >