RESUMO
Our biomimetic hypothesis proposes that families of diverse natural products with complex core structures such as 9,10-deoxytridachione, photodeoxytridachione and ocellapyrone A are derived in nature from a linear and conformationally strained all-( E) tetraene-pyrone precursor. We therefore synthesized such a precursor and investigated its biomimetic transformation under a variety of reaction conditions, both to the above natural products as well as to diverse isomers which we propose to be natural products "yet to be discovered". We also report herein the first synthesis of the natural product iso-9,10-deoxytridachione.
Assuntos
Produtos Biológicos/síntese química , Macrolídeos/química , Pironas/síntese química , Modelos Moleculares , Estrutura Molecular , Propionatos/química , Propionatos/metabolismoRESUMO
As part of our continuing studies of pyrone-containing natural products, a series 6-methoxypyran-2-ones were synthesized. These were found to react with molecular oxygen at 20 degrees C, and this novel reaction yielded a series of highly functionalized alpha,beta-butenolides. [reaction: see text]
RESUMO
A tandem Suzuki-coupling/electrocyclisation reaction sequence was employed for the biomimetic synthesis of (+/-)-9,10-deoxytridachione.
Assuntos
Biomimética , Propionatos/síntese química , Pironas/síntese química , Estrutura Molecular , Oceanos e Mares , Propionatos/química , Pironas/químicaRESUMO
The crispatenes and SNF4435 C&D are complex polypropionate derived natural products. The core structures of these compounds along with a complex unnatural structure can be easily prepared from a common polyene precursor simply by variation of the reaction conditions. The reaction pathways provide insight into the biosynthesis of these complex natural products.