SYNTHESIS OF NEW CONDURITOL ANALOGS DERIVED FROM BICYCLOOCTATRIENE - BIS-HOMO-CONDURITOL-D AND BIS-HOMO-CONDURITOL-F

KARA Y., BALCI M., BOURNE S., WATSON W.

TETRAHEDRON LETTERS, cilt.35, sa.20, ss.3349-3352, 1994 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 35 Sayı: 20
  • Basım Tarihi: 1994
  • Doi Numarası: 10.1016/s0040-4039(00)76904-8
  • Dergi Adı: TETRAHEDRON LETTERS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.3349-3352
  • Atatürk Üniversitesi Adresli: Evet

Özet

The first synthesis of conduritol analogues 2 and 3 is reported. The key compound 7 reacted with KMnO4 and m-chloroperbenzoic acid in a stereospecific manner to give syn-addition products 9 and 10, respectively. Zinc-dust elimination of 10 followed by epoxide opening resulted in the formation of 3b. The free tetrol 3 was obtained by ammonolysis. The other tetrol isomer 2 was obtained by similar synthetic steps.