Stereoselective Total Synthesis of (+/-)-Dasycarpidol and (+/-)-Dasycarpidone

Patir S., Tezeren M. A., SALİH B., Erturk E.

SYNTHESIS-STUTTGART, cilt.48, sa.23, ss.4175-4180, 2016 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 48 Sayı: 23
  • Basım Tarihi: 2016
  • Doi Numarası: 10.1055/s-0035-1562528
  • Dergi Adı: SYNTHESIS-STUTTGART
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.4175-4180
  • Hacettepe Üniversitesi Adresli: Evet

Özet

The protecting-group-free and scalable total syntheses of (+/-)-dasycarpidol and (+/-)-dasycarpidone, as well as the formal total synthesis of (+/-)-uleine, are presented starting from a common tetrahydro-carbazole-fused lactone that is conveniently prepared on multigram scale. The key azocino[4,3-b]indole skeleton is constructed via the DDQ-mediated dehydrogenative cyclization of a tetrahydrocarbazole derivative possessing an amide side chain. The syntheses of the target natural products are accomplished in high yields and in a few steps by employing readily available conventional reagents.