Dihydrocinnamoyl chloride

Starting with intermediate 145 (Scheme 26), 147 was prepared using dihydrocinnamoyl chloride, followed by catalytic hydrogenation and saponification of the ester group. The cyclization step was performed in the same manner as described above (see Scheme 27). The resulting product 148 was identical to the analogous derivative obtained from natural periphylline therefore, periphylline must possess structure 138 (775). The chirality of center-11 has been defined as S by ORD measurement in relation to the alkaloids chaenorhine and homaline (113). 

---