Journal
ORGANIC LETTERS
Volume 7, Issue 19, Pages 4289-4291Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol051799s
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- NIGMS NIH HHS [R01 GM071779] Funding Source: Medline
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An application of the phosphine-catalyzed [4 + 2] annulation in the formal synthesis of alstonerine and macroline is reported. A phosphine catalyzed [4 + 21 reaction between imine 7a and allene 8 formed the D ring of the target indole alkaloids. A subsequent intramolecular Friedel-Crafts acylation provided the C ring of the bridged tetracycle. Deprotection, followed by methylation of the bridged nitrogen, deoxygenation of the C6 ketone, and reduction of the C16 carbethoxy group provided the previously known intermediate 3.
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