海洋天然产物Urceolatin的全合成研究-有机化学专业论文.docxVIP

兰州人学硕上学位论文(2010)Abstract 兰州人学硕上学位论文(2010) Abstract This thesis aims at the studies on design of the total synthetic route of Urceolatin(P 1)，a component from a marine algae extract，including the study on the synthesis of the asymmetric stilbenes，which are key intermediates of P 1，and the study on the photocyclization reaction to yeild the precursor of phenanthro[4，5-bed]furan structured molecules．This thesis consists of the following two chapters： Chapter 1．Studies on the Total Synthesis of Urceolatin By imitating the biogenetic route of P 1，a convergent synthetic route has been designed． The details of the route are as follows：From commercially available reangents， p-hydroxyphenylaldehyde，Protocatechuic aldehyde，and Gallic acid，to produce three key segments respectively．Then by Wittig reaction of two segments of the three (aldehyde segment and WiRig reangent segment)to yeild a series of asymmetric stilbenes，which is under irradiation to yeild the phenanthrene derivatives，as a key precursor of phenanthro[4，5-bcd]furan structure，then by furan ring-closing reaction and Grignard reaction with the last segment(Grignard reangent segment)to synthesize the final product P 1，the above mentioned work is ongoing till now．We have completed 1 2 steps of the synthesis(The total synthetic route is constitueted by 1 9 steps)，including Wittig reaction，photocyclization reaction(two key steps)．And 39 compounds，among which 6 are new ones，have been synthesized with reletive spectra data． Chapter 2．Studies on the Stilbenes Derivatives as Key Intermediates of P1 With the brief review of the methods for making stilbenes，Wiaig reaction has been chosen as the key coupling step finally．And a systematic study has been taken on this step．By the experiments results of Wittig reactions，an optimalized route and proper conditions have been decided，then a series of stilbenes have been made，which are precursor of the photocyclization reaction． Keywords：Urceolatin；stilbene；phenanthro[4，5·bcd]furan；ph