.5,6 - Dihydrotestosterone Partial Promise Diosgenin Synthesis Research

Resource Chemistry is one of the most important research field in our group. The one of the most important tasks of our group is exploring the reaction of a great deal of resource compounds and their application in the synthesis of medicine, agricultural agents and natural product with potential bioactivity in order to realize the rational and high efficient utilization of the abundant resource compounds in our country and the elimination of excess waste. My dissertation is concerted on the synthesis of 5,6-dihydrogen Pennogenin by utilizing the intact skeleton of Tigogenin.For the synthesis of the 5, 6-dihydrogen Pennogenin, the Tigogenin was protected at C-3, followed the oxidation by Oxone at C-16 to afford the C-3 protected 16-hydroxyltigogenin. The latter reacted with HSCH2CH2SH to directly produced compound 3. The compound 3 suffered LiAlH4 reduced ketone at C-3, 22 . The 16-thioketal was converted to 16(17) double bond visa a series of reaction including 16-thioacetal opening and desulfurization with Raney nickel. After deprotection of Ac group and epoxidation to afford an important intermediate compound 8.The reactions of compound 8 with different acids have been investigated. Compound 8 can be transformded into 18-rearranged product 8-2-2 under the codition of boron trifluoride-ether. Apart product 8-2-2, also to get rearranged dehydrogrnated product under the condition of camphor acid.