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


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

SYNTHESIS-STUTTGART, vol.48, no.23, pp.4175-4180, 2016 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 48 Issue: 23
  • Publication Date: 2016
  • Doi Number: 10.1055/s-0035-1562528
  • Title of Journal : SYNTHESIS-STUTTGART
  • Page Numbers: pp.4175-4180

Abstract

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.