485801-60-3Relevant academic research and scientific papers
Cationic cyclization of 2-alkenyl-1,3-dithiolanes: Diastereoselective synthesis of trans-decalins
Goncalves, Sylvie,Santoro, Stefano,Nicolas, Marc,Wagner, Alain,Maillos, Philippe,Himo, Fahmi,Baati, Rachid
, p. 3274 - 3285 (2011/06/25)
An unprecedented and highly diastereoselective 6-endo-trig cyclization of 2-alkenyl-1,3-dithiolanes has been developed yielding trans-decalins, an important scaffold present in numerous di- and triterpenes. The novelty of this 6-endo-trig cyclization stan
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 (2007/10/03)
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.
