Tetrahedron Letters p. 1693 - 1696 (1997)
Update date:2022-07-30
Topics:
Wu, Michael H.
Jacobsen, Eric N.
An efficient formal synthesis of balanol is described. The thirteen-step sequence features a highly enantioselective (92% ee) ring opening of 1,4-cyclohexadiene monoepoxide with TMSN3 catalyzed by the Cr-salen complex 3. A selective Beckmann rearrangement followed by amide reduction and nitrogen functionalization affords 2, thus completing a formal synthesis of balanol in 31% overall yield.
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