Studies towards the total synthesis of (-)-lemonomycin | Posted on:2007-04-03 | Degree:Ph.D | Type:Thesis | University:Colorado State University | Candidate:Chen, Yuyin | Full Text:PDF | GTID:2451390005985252 | Subject:Chemistry | Abstract/Summary: | | An asymmetric synthesis of the tetracyclic core of (-)-lemonomycin is presented. It features an efficient route towards a highly versatile tetrahydroisoquinoline intermediate, in which a diastereoselective Pictet-Spengler reaction has been developed.; In addition, a novel oxidation was discovered in the process of an azomethine ylide cyclization for construction of C and D rings of lemonomycin. An investigation into the mechanism of this novel oxidation has been carried out and the results discussed. The tetracyclic enamide from this process represents a highly functionalized and versatile intermediate. Interestingly, the enamide double bond proved very resistant to reduction and this transformation was fully investigated. More recently, with high-pressure hydrogenation equipment, promising leads towards hydrogenation of this enamide have been uncovered. | Keywords/Search Tags: | Towards | | Related items |
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