485801-59-0Relevant academic research and scientific papers
Asymmetric tandem additions to chiral 2,3-dihydronaphthyloxazolines: Synthesis of the triptoquinone/triptinin a ring system
Basil, Laura F.,Nakano, Hiroto,Frutos, Rogelio,Kopach, Michael,Meyers
, p. 2064 - 2074 (2002)
A study to reach the diterpenoid (+)-triptoquinone A (3) or its analog (+)-triptinin A (4) via an asymmetric tandem addition to naphthyloxazolines is described. The tandem addition to the chiral dihydronophthalene 6 resulted in a 70% yield of a single diastereomer 10. Further manipulation gave the natural products' tricyclic ring system, compounds 20 and 29 via ring-closing metathesis in 90% yield, using the Schrock catalyst. Final assault to the target compounds 3 or 4 fell short due to the failure to either reduce a neopentyl hydroxymethyl group to a methyl or to install the conjugated carboxylic acid present in 3 or 4.
