Sequential exo-mode oxacyclizations for the synthesis of the CD substructure of brevenal.
J Antibiot (Tokyo)
; 72(6): 364-374, 2019 06.
Article
en En
| MEDLINE
| ID: mdl-30607013
ABSTRACT
We describe a novel strategy for synthesizing the CD bicyclic ether substructure of the fused polycyclic ether natural product brevenal. This product arises from a three-step sequence beginning with (1) regio- and diastereoselective iodoetherification of an acyclic diene-diol, followed by (2) alkene metathesis with an epoxyalkene synthon, concluding with (3) palladium-catalyzed cycloisomerization. Despite the modest yield and long reaction period for the cycloisomerization step, these studies provide valuable insights into the nature of byproducts generated and the mechanisms by which they form. This work demonstrates a portion of a larger synthetic strategy for constructing the pentacyclic core of brevenal from an acyclic precursor.
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Colección:
01-internacional
Banco de datos:
MEDLINE
Asunto principal:
Polímeros
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Idioma:
En
Revista:
J Antibiot (Tokyo)
Año:
2019
Tipo del documento:
Article
País de afiliación:
Estados Unidos