Synthesis of Multisubstituted Pyridines by Heterocyclization of TosMIC Derivatives: Total Synthesis of Caerulomycins A and K
José A. García-García, José Luis Aceña, Patricia García-García, David Sucunza
TL;DR
This paper presents a new method to efficiently create complex pyridine compounds using TosMIC derivatives, demonstrated by synthesizing caerulomycins A and K in just five steps.
Contribution
A novel tandem heterocyclization method using TosMIC derivatives for multisubstituted pyridine synthesis is introduced.
Findings
The method works with various electrophiles and mild conditions.
Caerulomycins A and K were synthesized in five steps from TosMIC.
The isocyanide group's dual reactivity enables efficient heterocyclization.
Abstract
A concise synthesis of multisubstituted pyridines from α-allylic TosMIC derivatives and electrophiles is reported. The process involves a tandem heterocyclization exploiting the dual reactivity of the isocyanide group. The methodology tolerates various electrophiles, including halogen sources, and proceeds under mild conditions. Its utility is showcased in the total synthesis of caerulomycins A and K, in only five steps from TosMIC.
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Taxonomy
TopicsCatalytic C–H Functionalization Methods · Coordination Chemistry and Organometallics · Multicomponent Synthesis of Heterocycles