PDF herunterladen
Synlett 1995; 1995(3): 263-266
DOI: 10.1055/s-1995-4936
letter
© 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.

Benzyne-Furan Cycloaddition Approach to the Angucyclines: First Total Synthesis of Antibiotic C104

Takashi Matsumoto, Tsukasa Sohma, Hiroki Yamaguchi, Shin Kurata, Keisuke Suzuki*
  • *Department of Chemistry, Keio University, Hiyoshi, Kohoku-ku, Yokohama 223, Japan
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
31. Dezember 2000 (online)

  als PDF herunterladen  Lizenzen und Reprints Alle Artikel dieser Rubrik

This paper describes the first total synthesis of an angucycline-class antibiotic, C104 (1), by exploiting regioselective benzyne-furan cycloaddition. Angularly fused α-siloxyfuran 3, generated in situ by treatment of butenolide 2 with NaH-TBDMSCl in THF, was directly subjected to the reaction with α-alkoxybenzyne 5, which was generated also in situ from α-iodo triflate 4. The high head-to-head selectivity in the mode of the cycloaddition enabled the regiocontrolled construction of the characteristic benz[a]-anthraquinone framework. The D-olivosyl C-glycoside was introduced via the O→C-glycoside rearrangement. This synthesis determined the absolute stereochemistry of this compound.

Benzyne-furan cycloaddition - Total synthesis - The angucyclines - Benz[a]anthraquinone - Aryl C-glucoside