Pancratistatin 7-deoxypancratistatin

Hudlicky, T., Tian, X., Konigsberger, K., Mauiya, R., Rouden, J. and Fan, B. (1996c) Toluene-dioxygenase-mediated as-dihydroxylation of aromatics in enantioselective synthesis. Asymmetric total syntheses of pancratistatin and 7-deoxypancratistatin, promising antitumor agents. J. Am. Chem. Soc., 118, 10752-10765. 

Since the isolation and discovery of the significant biological activity of 7-deoxypancratistatin (210) and pancratistatin (211), which have more oxygenated functional substituents than lycoricidine (204), synthetic studies have been performed extensively. The total synthesis of optically active (-1-)-7-deoxypancratistatin (210) and (+)-pancratistatin (211) has been reported independently by four research groups. 

The known conduritol 69 (Vol. 25, p. 210, ref. 66) has been used in synthetic studies directed towards the anticancer agent (+)-pancratistatin. See also Chapter 24 for the syntheses of (+)-pancratistatin and (+)-7-deoxypancratistatin involving the use and formation of cyclitols. 

Several members of the Amaryllidaceae family of alkaloids display pronounced biological activities, and some Amaryllidaceae plants have played an important role in traditional herbal medicine for the treatment of various ailments. The most prominent examples of Amaryllidaceae alkaloids of biological relevance are narciclasine (55) and its congeners (pancratistatin and 7-deoxypancratistatin) and galantamine (62) (also commonly spelled galanthamine). These natural products also find application in modem medicine, and in this respect, pancratistatin is used in clinical... 

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