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SmI2-mediated Radical Cross-couplings Of α-hydroxylated Aza-hemiacetals And N,S-acetals With α,β-unsaturated Compounds: Asymmetric Synthesis Of (+)-hyacinthacine A2, (-)-uniflorine A, And (+)-7-epi-casuarine.

Xuekui Liu, Shi Qiu, Yong-Gang Xiang, Yuan-Ping Ruan, X. Zheng, P. Huang
Published 2011 · Chemistry, Medicine

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The SmI(2)-mediated radical coupling reactions of β-hydroxylated pyrrolidine/piperidine aza-hemiacetals 8 and 9 and N,S-acetals 6 and 33 with α,β-unsaturated compounds are described. This method allows a rapid access to β-hydroxylated pyrrolidines, piperidines, pyrrolizidinones, and indolizidinones. Starting from N,S-acetal 33 and via a common intermediate 27, the alkaloids hyacinthacine A(2) (2), uniflorine A (3, 6-epi-casuarine), and the unnatural epimer 7-epi-casuarine (37) have been synthesized in four and five steps with overall yields of 34%, 16%, and 13%, respectively. The radical mechanism of the coupling reactions has been confirmed by controlled experiments, which also allowed deducing the anionic mechanism in the coupling between N,S-acetal 6 and carbonyl compounds. This demonstrates that the mechanisms of these SmI(2)-mediated reactions are switchable from Barbier-type anionic to radical by cooperative action of BF(3)·OEt(2) and t-BuOH.
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