Polysubstituted Piperidines via Iodolactonization: Application to the Asymmetric Synthesis of (+)-Pseudodistomin D
- 14 March 2012
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 14 (7), 1672-1675
- https://doi.org/10.1021/ol300209s
Abstract
Conjugate addition of lithium (S)-N-allyl-N-(α-methyl-p-methoxybenzyl)amide to methyl (E,E)-hepta-2,5-dienoate furnished the corresponding β-amino ester. N-Protecting group manipulation, ring-closing metathesis, and ester hydrolysis gave enantiopure [N(1′)-tert-butoxycarbonyl-1,2,3,6-tetrahydropyridin-2′-yl]ethanoic acid. Subsequent iodolactonization gave a bicyclic iodolactone scaffold. This key intermediate was elaborated to (+)-pseudodistomin D [in >99% ee and 7% yield over 16 steps from methyl (E,E)-hepta-2,5-dienoate].Keywords
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