Journal
ORGANIC LETTERS
Volume 8, Issue 8, Pages 1661-1664Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol0602506
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Funding
- NIGMS NIH HHS [R01 GM052491, R01 GM052491-04S1, R01 GM052491-04, GM-52491, R01 GM052491-05A1, R01 GM052491-06, R01 GM052491-07] Funding Source: Medline
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A formal synthesis of the Aspidosperma alkaloids aspidospermidine, aspidospermine, and quebrachamine is reported through an efficient preparation of Stork's penultimate intermediate. The key step of the sequence involved an intramolecular [3 + 2] cycloaddition of the 2-azapentadienyllithium 21 formed in situ from the corresponding imine 1, which after N-alkylation of the resulting cycloadduct provided 2 in excellent yield. The synthesis represents a new disconnection of the classical tricyclic ketone used for appendage of the requisite indole.
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