Ugi-4-component reaction enabling rapid access to the core fragment of massadine.
A rapid method to access the densely functionalized core structure of massadine (1) has been developed. The use of the Ugi-4-component reaction involving a convertible isonitrile and an end-group differentiating ozonolysis constitute the key operations toward the synthesis of the D-ring subunit.
Laboratorium für Organische Chemie, ETH Zürich, CH-8093 Zürich, Switzerland.
Gary M
GM
Chinigo
Alexander
A
Breder
Erick M
EM
Carreira
D006571:Heterocyclic Compounds / Q000737:chemistry; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013997:Time Factors
C503429:1,2,4-trioxane; D006571:Heterocyclic Compounds; D011758:Pyrroles; C478874:massadine