New gold-catalyzed reactions and applications for the synthesis of alkaloids

Identifier:  TDX:1234

Handle: https://hdl.handle.net/20.500.11797/TDX1234

Authors:  Escribano Cuesta, Ana

Abstract:
During this Doctoral Thesis a detailed study of the inter- and intramolecular reactions of carbonyl compounds with 1,6-enynes using gold(I) complexes were developed, streamlining the variables that allow the selective synthesis of different products, such as tricyclic compounds, dihydropyrans, 1,3-dienes or cyclobutenes. Given the importance and difficulty of synthesizing compounds bearing a cyclobutene subunit, in the second chapter the preparation of products is described, which include a bicyclo[3.2.0]hept-5-ene motif, via gold-catalyzed cycloisomerization of 1,8-enynes. In the last chapter, the main core of lundurines has been synthesized by appling the methodology developed in the group for the intramolecular gold-catalyzed cyclization of indoles with alkynes. Lundurines are a new type of indole alkaloids, which are characterized by an unusual carbon skeleton. Interestingly, lundurines B and D have shown significant in vitro cytotoxicity toward B16 melanoma cells.