A novel and stereospecific synthesis of aminocyclitol: N-tosyldihydroconduramine E2

Kelebekli L., ÇELİK M., KARA Y.

JOURNAL OF CHEMICAL RESEARCH, sa.1, ss.54-56, 2010 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Basım Tarihi: 2010
  • Doi Numarası: 10.3184/030823410x12628681698796
  • Dergi Adı: JOURNAL OF CHEMICAL RESEARCH
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.54-56
  • Anahtar Kelimeler: N-tosyldihydroconduramine E2, conduramine, aminocyclitol, endoperoxide, AMINOCYCLOPENTITOL GLYCOSIDASE INHIBITORS, ASYMMETRIC INDUCTION, RADICAL CYCLIZATION, CYCLITOLS, PURE
  • Atatürk Üniversitesi Adresli: Evet

Özet

A stereospecific synthesis of N-tosyldihydroconduramine E2, a new aminocyclitol, has been synthesised starting from cyclohexa-1,3-diene. The photooxygenation of cyclohexa-1,3-diene afforded the bicyclic endoperoxide. Reduction of the endoperoxide with thiourea and then reaction of the bis-carbamate with p-TsNCO followed by a palladium-catalysed ionisation/cyclisation reaction, gave a vinyl oxazolidin-2-one. Oxidation of the double bond in the oxazolidin-2-one with KMnO(4) followed by acetylation, gave the oxazolidinone-diacetates. Hydrolysis of the oxazolidinone ring and removal of the acetate groups gave the desired aminocyclitol, N-tosyldihydroconduramine E2.