Enantioselective Total Syntheses of (-)-Isonitramine, (-)-Sibirine, and (+)-Nitramine by Ring-Closing Metathesis

[摘要]：Concise enantioselective total syntheses of naturally occurring 2-azaspiro[5,5]undecan-7-ol (Nitraria) alkaloids viz. ()-isonitramine, ()-sibirine, and (+)-nitramine are accomplished in 42, 38, and 25?% overall yield, respectively, in six steps starting from enantiomerically pure (S)-methyl 3-allyl-2-oxo-1,2,3,6-tetrahydropyridine-3-carboxylate (>99?%?ee). The key feature of the syntheses involves diastereoselective HosomiSakurai allylation followed by ring-closing metathesis.

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