ピロリジジンアルカロイドおよびリグナンラクトングリコシド制癌物質の合成と生理活性

エナンチオ, ジアステレオ異性体の観点より

抄録

This article describes the syntheses and the relationships between structure and antitumor activity of pyrrolizidine alkaloid (indicine N-oxide), lignan lactone glycoside (etoposide) and their related compounds from the standpoint of diastereomer and enantiomer.
Total syntheses of indicine N-oxide, its diastereomer (intermedine N-oxide) and their enantiomers have been achieved in a totally stereospecific fashion through a sequence involving as the key steps (a) the enantioselective synthesis of retronecine and its enantiomer, (b) the enantioselective synthesis of (+) -trachelanthic acid and its enantiomer, and (c) a combination of each segments.
Syntheses of all four possible diastereomers of etoposide and its aminoglycosidic analogues have been achieved via optical resolution of (±) -podophyllotoxin by glycosidation with D- and L-sugars.