An efficient regioselective and diastereoselective synthesis of the epoxy-quinol functionality as building block for the manumycin antibiotics by the sequence of photooxygenation, reduction and Weitz-Scheffer epoxidation

Adam W., Kilic H., Saha-Moller C.

SYNLETT, sa.3, ss.510-512, 2002 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Basım Tarihi: 2002
  • Dergi Adı: SYNLETT
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED)
  • Sayfa Sayıları: ss.510-512
  • Anahtar Kelimeler: photooxygenation, quinol, Weitz-Scheffer epoxidation, diastercoselectivity, regioselectivity, FAMILY, LL-C10037-ALPHA, BIOSYNTHESIS, ANALOGS
  • Atatürk Üniversitesi Adresli: Hayır

Özet

The photooxygenation of the acetanilide 2 affords the hydroperoxide 3, which by titanium-tetraisopropoxide-catalyzed reduction with dimethyl sulfide gives the corresponding quinol 4. Regioselective and diastereoselective Weitz-Scheffer epoxidation of the latter by tert-butyl hydroperoxide (TBHP) and DBU as base catalyst leads to the cis-epoxy quinol 1, the essential functionality in Manumycin antibiotics.