Tetrahedron Letters p. 2643 - 2647 (2000)
Update date:2022-08-17
Topics:
Miyazaki, Hidekazu
Honda, Yoshinari
Honda, Kiyoshi
Inoue, Seiichi
5-(Phenylthio)pyrano[3,2-c][1]benzopyrans (6) were successfully synthesized in high yield by the reaction of 5-phenylthio-4-penten-1-ol (5) and salicylaldehyde (1) in benzene in the presence of p-toluenesulfonic acid and trimethyl orthoformate, trans,trans-Isomer 6a and cis,cis-isomer 6d were produced as major products from (E)5 and (Z)-5, respectively. Treatment of 6a with lithium 4,4'-di-tert-butylbiphenyl or Raney Ni (W-4) lead to trans- pyrano[3,2-c][1]benzopyran 4b which is very difficult to make by direct cycloaddition using unsubstituted 4-penten-1-ol (2b). (C) 2000 Elsevier Science Ltd.
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