Total Synthesis of Brazilin
2015
Jung, Youngeun | Kim, Ikyon
Described herein is a highly efficient total synthesis of brazilin from commercially available starting materials in 9 steps with 70% overall yield. Mitsunobu coupling followed by In(III)-catalyzed alkyne–aldehyde metathesis allowed for rapid construction of brazilin core skeleton in quantitative yield. Subsequent modulation of oxidation levels and acid-catalyzed cyclization led to the trimethyl ether of brazilin. Asymmetric dihydroxylation of the key intermediate was also demonstrated, which would permit asymmetric access to (+)-brazilin.
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