4.8 Article

Total Synthesis of (-)-Leuconicine A and B

Journal

ORGANIC LETTERS
Volume 13, Issue 17, Pages 4736-4737

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol202056w

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Funding

  1. Cephalon, Inc.

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Concise asymmetric total syntheses of Strychnos alkaloids (-)-leuconicine A (14 steps, 9% overall yield) and B (13 steps, 10% overall yield) have been accomplished. Key steps include (1) our sequential one-pot spiro-cyclization/intramolecular aza-Baylis-Hillman method to prepare the ABCE framework; (2) a novel domino acylation/Knoevenagel cyclization to prepare the F-ring; and (3) a Heck cyclization to access the D-ring.

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