Download PDF
Synthesis 1995; 1995(9): 1142-1146
DOI: 10.1055/s-1995-4052
paper
© 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.

Studies of the Furan-Terminated Cationic Cyclization: A Serendipidious Synthesis of Pallescensin A

Udo Lange, Siegfried Blechert*
  • *Institut für Organische Chemie, Sekretariat C3, Technische Universität Berlin, Straße des 17. Juni 135, D-10623 Berlin, Germany, Fax +49(30)31423619
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

The furan-terminated cationic cyclization reaction of 4-(2-furan-2-yl-2-methoxyethyl)-3,5,5-trimethylcyclohex-2-enol (3) yielded 6,6,9a-trimethyl-4,5,5a,6,7,9a-hexahydronaphtho[1,2-b]furan-4-ol (9b) in a Pictet-Spengler-like reaction thereby giving a good insight into the possible mechanism of this β-cyclization. Alcohol 9b was converted into 6,6,9a-trimethyl-7,9a-dihydro-6H-naphtho[1,2-b]furan-4-one (12), thus, completing a formal total synthesis of pallescensin A (13).

furan derivatives - cationic cyclization - pallescensin A