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Synlett 1996; 1996(7): 682-684
DOI: 10.1055/s-1996-5549
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Synthesis of [7.3.2]-Enediynes

Martin E. Maier* , Diane Langenbacher
  • *Martin-Luther-Universität Halle-Wittenberg, Fachbereich Chemie, Institut für Organische Chemie, Kurt-Mothes-Str. 2, 06120 Halle (Saale), Germany, FAX: (+49) 345 55 270 28, e-mail: maier@chemie.uni-halle.de
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Publication Date:
31 December 2000 (online)

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Addition of acetylide to the seven-membered ketone 5, followed by construction of the enediyne bow, provided access to the enediyne aldehyde 15. Treatment of the aldehyde 15 with KN(SiMe3)2 and trapping of the intermediate alkoxide furnished the [7.3.2]enediyne 16 with a bridgehead double bond. Hydroboration of 16 allowed the functionalization of the two-carbon bridge to give the enediyne 17. Both enediynes proved to be stable upon heating in CCl4 for several hours.

enediynes - macrocycles - [7.3.2]enediyne - force-field calculations

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