Synthesis of tricyclic ring systems: [2+2] ketene addition reaction for preparation of tricyclic ketone, alcohol, and lactone derivatives

Yilmaz O., Bekfelavi E. Y., Kus N. S., Tunc T., ŞAHİN E.

CHEMICAL PAPERS, cilt.71, sa.5, ss.929-938, 2017 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 71 Sayı: 5
  • Basım Tarihi: 2017
  • Doi Numarası: 10.1007/s11696-016-0013-7
  • Dergi Adı: CHEMICAL PAPERS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.929-938
  • Anahtar Kelimeler: Ketene addition, Tricyclic molecules, Lactone, Ketone, NATURAL-PRODUCT-LIKE, STEREOSELECTIVE-SYNTHESIS, PRIVILEGED SYNTHONS, HALOLACTONES, LIGNAN, PHASE
  • Atatürk Üniversitesi Adresli: Evet

Özet

The addition of dichloroketene to 1,4-cyclohexadiene was examined. Dichloroketene, which was easily prepared from trichloroacetyl chloride and Zn-Cu, reacted with 1,4-cyclohexadiene in the presence of POCl3 to afford novel racemic products of single addition (5) and double addition (6). The adducts 6 and 7 were reacted separately with MCPBA (meta-chloroperbenzoic acid), H2O2, LiAlH4, and cis-diol 10 was reacted with PCC (pyridinium chlorochromate) to afford lactone, alcohol, and ketone derivatives likely to exhibit biological activity. The structures of all the racemic molecules mentioned in the article were determined from H-1 NMR, C-13 NMR, MS, and IR data.