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Synthesis of three generations of model substrates with advancing similarity to chatancin are presented. In the first two generations, an Ireland-Claisen based six-step sequence supplied the trans-dienophile to be connected by dithiane chemistry to furfurals. In the third generation, a homogeraniol based dienophile aldehyde was coupled with a dilithiated 3-furoic acid. Subsequently, all three generations...
Title investigation of three generations of model substrates targeting chatancin is presented. An unfunctionalized furan affords a reversible transannular Diels-Alder reaction producing only the two TAC-frameworks where the expected one is the kinetic product. A furan 3-COOMe functionalization allows the selective formation of the expected isomer which is still favored even in the presence of a...
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