81633-95-6Relevant academic research and scientific papers
A concise synthetic approach to the sorbicillactones: Total synthesis of sorbicillactone A and 9-epi-sorbicillactone A
Volp, Kelly A.,Johnson, Diane M.,Harned, Andrew M.
, p. 4486 - 4489 (2011)
A concise (12 step) total synthesis of sorbicillactone A and 9-epi-sorbicillactone A is reported. Unlike typical routes to the sorbicillinoids, this strategy does not start from sorbicillin and allows for the production of the bicyclic core on a multigram scale. The intramolecular conjugate addition of a tethered malonate serves as an effective means of introducing the lactone ring and provides a synthetic handle for installing the amide nitrogen.
Regioselective and stereoselective cyclizations of cyclohexadienones tethered to active methylene groups
Tello-Aburto, Rodolfo,Kalstabakken, Kyle A.,Volp, Kelly A.,Harned, Andrew M.
supporting information; experimental part, p. 7849 - 7859 (2011/12/04)
The cyclization of 2,5-cyclohexadienones tethered to activated methylene groups was studied. The substitution around the cyclohexadienone ring serves to regioselectively direct these cyclizations based primarily on electronic effects. In the case of brominated substrates, these reactions proceed to give highly unusual electron-deficient tricyclic cyclopropanes. By using a Cinchona alkaloid-based phase-transfer catalyst, prochiral cyclohexadienones can be desymmetrized with moderate stereoselectivity.
