Nuevas estrategias sintéticas orientadas a la obtención de fragmentos estructurales presentes en productos naturales

Abstract

This thesis focuses on the development of new synthetic strategies oriented to the obtaining of structural moieties found in natural products. Concretely, several oxygenated scaffolds have been deeply studied throughout different research lines. Firstly, a general and robust method for the synthesis of valuable vinyl ether was developed, and those structures were submitted to several transformations to achieve a varied family of derivatives. Secondly, the first total syntheses of natural products 2,6-(Z,E)-thymifodioic acid and bioactive 2,6-(E,E)-thymifodioic acid, as well as their two non-naturally occurring stereoisomers and their four dimethyl diester, was achieved. Thirdly, it was developed the first general method for the synthesis of treasured 2,3,4,5,6-pentasubstituted tetrahydropyrans; those structures were obtained, via a novel Evans Aldol-Prins (EAP) strategy, with good yields, excellent diastereoselectivities and allowing the introduction of a panoply of substituents and stereochemical patterns. Last but not least, several epoxy alcohols analogues to those found in natural products 15,16-epoxythyrsiferols A and B were synthesized, and also a battery of 2,4-disubstituted butenolides was prepared, employing in both cases methodologies developed by Sharpless.