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Synlett 2012; 23(9): 1327-1330
DOI: 10.1055/s-0031-1290937
letter
© Georg Thieme Verlag Stuttgart · New York

Synthetic Study of the Angular Tetracyclic Core Skeleton of Landmycine A via Masamune–Bergman Cyclization

Sho Yamaguchi
a   Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro, Tokyo 152-8552, Japan, Fax: +81(3)57342884   eMail: thiroshi@apc.titech.ac.jp
,
Hiroshi Tanaka*
a   Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro, Tokyo 152-8552, Japan, Fax: +81(3)57342884   eMail: thiroshi@apc.titech.ac.jp
,
Ryo Yamada
b   Department of Organic and Polymer Materials, Graduate School of Science and Engineering, Tokyo Institute of Technology 2-12-1-E4-6, ­Ookayama, Meguro, Tokyo 152-8552, Japan, eMail: skawauchi@polymer.titech.ac.jp
,
Susumu Kawauchi
b   Department of Organic and Polymer Materials, Graduate School of Science and Engineering, Tokyo Institute of Technology 2-12-1-E4-6, ­Ookayama, Meguro, Tokyo 152-8552, Japan, eMail: skawauchi@polymer.titech.ac.jp
,
Takashi Takahashi*
a   Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro, Tokyo 152-8552, Japan, Fax: +81(3)57342884   eMail: thiroshi@apc.titech.ac.jp
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Publikationsverlauf

Received: 13. Februar 2012

Accepted after revision: 13. März 2012

Publikationsdatum:
14. Mai 2012 (online)

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Abstract

We describe the synthesis, via Masamune–Bergman cyclization, of an angucycline derivative involving a quinone in the B ring and a nonaromatic hydroxylated C ring. The naphthoquinone was synthesized via the copper-catalyzed Ullmann reaction of the dihalo aryl moiety, and the subsequent oxidation of a corresponding hydroquinone. The aryl dihalide was prepared by the dihalogenation of the 1,4-diradical generated during the Masamune–Bergman cyclization of the 1,2- dialkynylbenzene under neutral conditions. This methodology suggests a new route for the construction of natural products containing an anthraquinone skeleton.

Key words

aglycon - deoxyoligosaccharide - quinone - NHK coupling - Ullmann coupling

Supporting Information

    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
  • Supporting Information
 

  • References and Notes

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