Microwave-assisted concise total syntheses of quinazolinobenzodiazepine alkaloids

J Org Chem. 2005 Dec 9;70(25):10488-93. doi: 10.1021/jo051876x.

Abstract

[reactions: see text] One-pot total syntheses of the quinazolinobenzodiazepine alkaloids sclerotigenin (1), (+/-)-circumdatin F (2), and (+/-)-asperlicin C (3) via novel microwave-assisted domino reactions were achieved in 55%, 32%, and 20% yields, respectively, from commercially available starting materials. A two-step total synthesis of (+/-)-benzomalvin A (4) was accomplished with an overall yield of 16%. Additionally, analogues of circumdatin E were synthesized via the three-component one-pot sequential reactions promoted by microwave irradiation. Finally, a two-step formal total synthesis of (+/-)-asperlicin E (5) was also realized by using this microwave-assisted protocol.

MeSH terms

  • Alkaloids / chemical synthesis*
  • Benzodiazepines / chemical synthesis*
  • Benzodiazepinones / chemical synthesis
  • Methods
  • Microwaves*
  • Pyrimidinones / chemical synthesis
  • Quinazolines / chemical synthesis*

Substances

  • Alkaloids
  • Benzodiazepinones
  • Pyrimidinones
  • Quinazolines
  • circumdatin F
  • Benzodiazepines
  • benzomalvin A
  • asperlicin E
  • asperlicin C