《mbine and Reserpine Alkaloids; Part 1.An Improved Synthesis of cis-5, 8-Dihydroxy-1, 4, 5, 8, 9,10-hexahydronaphthalene-1, 8-lactone via Selective Reduction of the Conjugated Ketone with Zn (BH4)2》.pdfVIP

Chinese Chemical Letters Vol. 15, No. 3, pp 265-268, 2004 265 /journal/ccl.html Toward Total Synthesis of Yohimbine and Reserpine Alkaloids; Part 1. An Improved Synthesis of cis-5, 8-Dihydroxy-1, 4, 5, 8, 9,10- hexahydronaphthalene-1, 8-lactone via Selective Reduction of the Conjugated Ketone with Zn (BH ) 4 2 Yong Ye LI, Mei XU, Fen Er CHEN* Department of Chemistry, Fudan University, Shanghai 200433 Abstract: An improved and high-yielding synthesis of cis-5, 8-dihydroxy-1, 4, 5, 8, 9, 10- hexa- hydronaphthalene-1,8-lactone 7, an intermediate for (-)-reserpine 1 is presented. The conjugated ketone 5 was regioselectively reduced to afford lactone 7 with zinc borohydride formed in situ from KBH and ZnCl in THF. 4 2 Keywords: (-)-Reserpine, lactone, zinc borohydride, reduction, synthesis . cis-5, 8-Dihydroxy-1, 4, 5, 8, 9, 10-hexahydronaphthalene-1, 8-lactone 7 is the key intermediate to build E ring 2 possessing five chiral centers in total synthesis of (-)-reserpine 11, 2. In 1958, Woodward firstly reported an artful route to the synthesis of (-)-reserpine from the acid 4. One major drawback of this promising approach is the low yield obtained in the synthesis of the required lactone 7. Herein, we described an efficient and improved method for the synthesis of 7 as shown in Scheme 1 .