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Published on: July 17, 2020
Total synthesis of (-)-senepodine G and (-)-cermizine C
Barry B Snider1, James F Grabowski
1Department of Chemistry, MS 015, Brandeis University, Waltham, Massachusetts 02454-9110, USA. snider@brandeis.edu
The Journal of Organic Chemistry
|January 27, 2007
Abstract:
An efficient, stereospecific synthesis of the alkaloids senepodine G (2) and cermizine C (1) has been completed using the BF3.Et2O-promoted stereospecific addition of Me2CuLi to alpha,beta-unsaturated lactam 6 to provide lactam 3, the addition of MeMgBr followed by HCl to convert 3 to senepodine G (2) (six steps, 40% overall yield), and the stereospecific NaBH4 reduction of 2 to give cermizine C (1) (seven steps, 40% overall yield).
