Savinin

Acanthopanax sessiliflorus (Rupr. et Maxim.) Seem. Duan Geng Wu Jia (root, bark) 1-Sesamin, savinin, acanthosides, syringaresinol, daucosterin, daucosterol.48 Diuretic, anti-inflammatory. 

Honda T, Kimura N et al (1994) Chiral synthesis of lignan lactones, (—)-hinokinin, (—)-deoxypodorhizone, (—)-isohibalactone and (—)-savinin by means of enantioselective deprotonation strategy. J Chem Soc Perkin Trans 1 1043-1046... 

In their review of lignans MacRae and Towers [9] cited the activity of kobusin and sesamin against silkworm larvae, sesamin and sesamolin against juvenile hormone activity in the milkweed bug, and podophyllotoxins against insect larval growth. On the other hand, sesamin, asarinin, savinin and hinokinin enhanced the toxicity of a wide variety of insecticides. 

Finally, several recent syntheses involve the preparation of aP unsaturated lactones of the savinin or gadain type. Such compounds are readily prepared from the corresponding monobenzyl-butyrolactones by condensation (scheme 19). While elimination of the mesylate leads to the (Z)- somex [71], elimination of the acetate affords the j-isomer [72]. The (Z)-isomer (61) can be converted into (-)-savinin (62) in high yield by treatment with tributyltin hydride. Hydrogenation of (61) or (62) affords the cw-disubstituted lactones (63) (scheme 20) [73]. 

J. Reisch, I. Novak, K. Szendrei and E. Minker, Savinin (hibalactone)... 

Scheme 3.30 Sequential Negishi alkenylation processes for the syntheses of savinin, gadain, and (+)-epolactaene [93c, 136].

Since the oxidative addition proceeds with retention of stereochemistry at the double bond, this chemistry can be used for the stereoselective synthesis of natural products like savinin or gadain (Scheme 5-80). ... 

Scheme 5-80. Cross-coupling of a-haloacrylates in the total synthesis of gadain and savinin. ...

---