RESUMO
Asymmetric total synthesis of (+)-gabosine C, (+)-pericosine B, and (+)-pericosine C has been reported from readily available d-(-)-isoascorbic acid and d-ribose involving Grubbs ring closing metathesis, Morita-Baylis-Hillman (MBH) reaction, and Luche reduction.
Assuntos
Carbaçúcares/síntese química , Cicloexanóis/síntese química , Cicloexanonas/síntese química , Ácido Chiquímico/análogos & derivados , Ácido Ascórbico/química , Catálise , Estrutura Molecular , Oxirredução , Ribose/química , Ácido Chiquímico/síntese química , EstereoisomerismoRESUMO
A simple and highly efficient protocol for pivaloylation of alcohols without using a catalyst under solvent-free conditions has been developed. The key advantages of the reaction are short reaction time, high yields, simple workup, and no need for further purification. Selectivity was observed between primary alcohols vs. secondary alcohols and aliphatic alcohols vs. aromatic alcohols. The accentuated and relevant phenomenon of this method that we observed is in one-pot conversion of TBS protection into Piv protection of the hydroxyl group.
