Journal
ORGANIC LETTERS
Volume 13, Issue 19, Pages 5216-5219Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol202101p
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Funding
- NIMH
- Lynde and Harry Bradley Foundation
- NIDA-NRL [Y1-DA1101]
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The optically active tetracyclic ketone 8 was converted into the pentacylic core 14 of the C-19 methyl substituted N-a-H sarpagine and ajmaline alkaloids via a critical haloboration reaction. The ketone 14 was then employed in the total synthesis of 19(S),20(R)-dihydroperaksine-17-al (1) and 19(S),20(R)-dihydroperaksine (2). The key regioselective hydroboration and controlled oxidation-epimerization sequence developed in this approach should provide a general method to functionalize the C(20)-C(21) double bond in the ajmaline-related indole alkaloids.
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