Volume 114, Issue 6 pp. 1104-1109
Zuschrift

Enantioselective Synthesis of Kedarcidin Chromophore Aglycon in Differentially Protected Form

Andrew G. Myers Prof.

Andrew G. Myers Prof.

Department of Chemistry and Chemical Biology Harvard University Cambridge, Massachusetts 02138 (USA) Fax: (+1) 617-495-4976

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Philip C. Hogan

Philip C. Hogan

Department of Chemistry and Chemical Biology Harvard University Cambridge, Massachusetts 02138 (USA) Fax: (+1) 617-495-4976

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Alexander R. Hurd

Alexander R. Hurd

Department of Chemistry and Chemical Biology Harvard University Cambridge, Massachusetts 02138 (USA) Fax: (+1) 617-495-4976

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Steven D. Goldberg

Steven D. Goldberg

Department of Chemistry and Chemical Biology Harvard University Cambridge, Massachusetts 02138 (USA) Fax: (+1) 617-495-4976

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Financial support from the National Institutes of Health is gratefully acknowledged. We thank Dr. Richard Staples and Mr. Andrew Haidle for the X-ray analysis of compound 20.

Graphical Abstract

Vier in Grammmengen hergestellte Komponenten wurden verknüpft bei der konvergenten (längste lineare Sequenz: 25 Stufen), enantioselektiven Synthese des komplementär geschützten Aglycons des Kedarcidin-Chromophors (1). Einer der Schlüsselschritte war eine transanulare anionisch induzierte Cyclisierung zum Bicyclo[7.3.0]dodecadiendiin-Gerüst in Gegenwart eines überbrückten Makrolactons. MOM=Methoxymethyl, TIPS=Triisopropylsilyl, TES=Triethylsilyl.

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