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Synthesis 1993; 1993(2): 221-224
DOI: 10.1055/s-1993-25835
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The Oligoselective Syntheses of Polyacene Derivatives

Peter R. Ashton* , John P. Mathias, J. Fraser Stoddart
  • *School of Chemistry, University of Birmingham, Edgbaston, Birmingham B15 2TT, England
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Publication Date:
17 September 2002 (online)

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The synthesis of the undecacene derivatives rel-(1R, 4S, 6R, 6aR, 8S, 10S, 11aR, 12R, 14S, 17R, 19S, 19aS, 21R, 23R, 24aS, 25S)-1,4 : 6,25 : 8,23 : 10,21 : 12,19 : 14,17-hexaepoxy-1,4,6,6a.7,8, 10,11,11a,12,14,17,19,19a,20,21,23,24,24a, 25-eicosahydroundecacene (6) and rel-(1R, 4S, 6S, 6aS, 8R, 10R, 11aS, 12S, 14S, 17R, 19R, 19aR, 21S, 23S, 24aR, 25R)-1,4 : 6,25 : 8,23 : 10,21 : 12,19 :14,17-hexaepoxy-1,4,6,6a,7,8,10,11,11a,12,14,17,19,19a,20,21,23,24,24a, 25-eicosahydroundecacene (7) are reported. The initial stages of a reaction sequence in which thermally-promoted and high pressure-promoted cycloadditions between the anti-bisdienophile 1a and the bisdiene 4 are used alternately to obtain the polyacene derivatives rel-(1R, 4S, 5aS, 6S, 8S, 8aS, 10S, 13R, 14aR, 15R, 17R, 17aR)-1,4 : 6,17 : 8,15 : 10,13-tetraepoxy-1,4,5,5a,6,8,8a,9,10,13,14,14a,15,17,17a,18-hexadecahydro-2,3,10,11-tetramethylideneheptacene (8) and rel-(1R, 4S, 6S, 6aS, 8S, 9aR, 10R, 12R, 12aR, 14S, 15aS, 16S, 18S, 21R, 23R, 23aR, 25R, 26aS, 27S, 29S, 29aS, 31R, 32aR, 33R)-1,4 : 6,33 : 8,31 : 10,29 : 12,27 : 14,25 : 16,23 : 18,21-octaepoxy-1,4,6,6a,7,8,9,9a, 10,12, 12a,13,14,15,15a,16,18,21,23,23a,24,25,26,26a,27,29,29a,30,31,32,32a,33-dotriacontahydropentadecacene (9) with complete oligoselectivity and treble diastereoselectivity in each step are described.

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