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Total synthesis of (-)-senepodine G and (-)-cermizine C.

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).

SUBMITTER: Snider BB

PROVIDER: S-EPMC2515611 | biostudies-literature | 2007 Feb

REPOSITORIES: biostudies-literature

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Total synthesis of (-)-senepodine G and (-)-cermizine C.

Snider Barry B BB Grabowski James F JF

The Journal of organic chemistry 20070201 3

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). ...[more]

PMID: 17253832

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