Diastereoselective Reductive Ring Expansion of Spiroketal Dihydropyranones to cis-Fused Bicyclic Ethers

Zhu, Liangyu; Song, Liyan; Tong, Rongbiao

Diastereoselective Reductive Ring Expansion of Spiroketal Dihydropyranones to cis-Fused Bicyclic Ethers

2012

Zhu, Liangyu | Song, Liyan | Tong, Rongbiao

A novel double cascade synthetic strategy was developed for the diastereoselective syntheses of cis-fused bicyclic ethers, featuring cascade Achmatowicz rearrangement/spiroketalization and cascade spiroketal reduction/oxa-Michael cyclization. Especially, the chemo-, regio-, and diastereoselective reduction of densely functionalized spiroketal dihydropyranones, followed by oxa-Michael cyclization in a one-pot fashion, was achieved.

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