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Published September 14, 2007 | Supplemental Material
Journal Article Open

Convergency and Divergency as Strategic Elements in Total Synthesis: The Total Synthesis of (−)-Drupacine and the Formal Total Synthesis of (±)-Cephalotaxine, (−)-Cephalotaxine, and (+)-Cephalotaxine


A concise route toward the syntheses of (−)-drupacine and (+)- and (−)-cephalotaxine has been developed. The syntheses rely on Pd(II)-catalyzed aerobic oxidative heterocyclization chemistry, which was employed to rapidly construct an important spirocyclic amine intermediate. A dynamic β-elimination/conjugate addition process was strategically applied to complete the first asymmetric total synthesis of (−)-drupacine.

Additional Information

© 2007 American Chemical Society. Received June 8, 2007; Publication Date (Web): August 18, 2007. We thank the NIH-NIGMS (R01 GM65961-01), Bristol-Myers Squibb Co. (graduate fellowship to E.M.F.), the NSF (graduate fellowship to E.M.F.), the Dreyfus Foundation, Merck Research Laboratories, Research Corporation, Abbott Laboratories, Pfizer, Amgen, GlaxoSmithKline, Lilly, and Johnson and Johnson for generous financial support. We are grateful to Ernie Cruz, Sandy Ma, and John Enquist for experimental assistance.

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