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Synlett 2011(2): 207-210
DOI: 10.1055/s-0030-1259288
DOI: 10.1055/s-0030-1259288
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthetic Studies Towards Crinine-Type Amaryllidaceae Alkaloids: Synthesis of (±)-Oxocrinine and Formal Synthesis of (±)-Crinine
Further Information
Publication History
Received
14 September 2010
Publication Date:
23 December 2010 (online)


Abstract
A flexible strategy leading to the synthesis of crinine-type Amaryllidaceae alkaloids, (±)-oxocrinine and (±)-crinine, has been developed. A notable feature in this synthetic route is the construction of tetrahydro-1H-benzo[c]azepine framework using an intramolecular Heck reaction and the formation of the sterically congested spiro cyclohexenone intermediate with a Robinson annulation.
Key words
Amaryllidaceae alkaloids - crinine - oxocrinine - total synthesis - quaternary carbon
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- Supporting Information