Investigation toward the Synthesis of a fragment of Carolin A


Moreno Caparrós, Neus


This study investigates the synthetic path of the bis-THF ring system and its neighboring β-hydroxy functions of carolin A, an acetogenin isolated from the seeds of Annona spinescens, which shows antitumoral properties amongst other pharmacological effects.
A 16-step synthetic route was carried out using modern synthetic organic chemistry, employing reactions like Johnson-Claisen rearrangement, Still-Gennari variation of the Horner-Wadsworth-Emmons reaction and a Sakurai-type reaction. Organic compounds were purified through column chromatography and distillation and, their structures were determined using of state-of-the-art analytical techniques (1H and 13C-NMR, COSY, HMBC, HSQC), IR, and MS. Ethyl (2Z,6E,10S,11S)-11-(hydroxy)-10-[(4-
methoxybenzyl)oxy]tetradeca-2,6,13-trienoate was the last compound synthesized in this project, starting from L-glutamic acid, and with an overall yield of 1%.



Cuenca González, Ana Belén
Stark, Christian B. W.


IQS SE - Undergraduate Program in Chemistry