ol0c00565_si_001.pdf (9.16 MB)
Construction of Polyfunctionalized 6–5–5 Fused Tricyclic Carbocycles via One-Pot Sequential Semipinacol Rearrangement/Michael Addition/Henry Reaction
journal contribution
posted on 2020-02-24, 22:43 authored by Fu-Ping Zhu, Xiang Guo, Fu-Min Zhang, Xiao-Ming Zhang, Hong Wang, Yong-Qiang TuA novel
one-pot semipinacol rearrangement/Michael addition/Henry
reaction of vinylogous α-ketols with nitroolefins has been achieved
through the promotion of two Lewis acids, namely, TMSOTf and TiCl4, at temperatures between 0 and −78 °C. A range
of synthetically challenging polyfunctionalized 6–5–5
and 7–5–5 fused tricyclic carbocycles bearing up to
five continuous stereocenters, including one quaternary carbon center,
are rapidly constructed in moderate to good yields with good to high
diastereoselectivities in most cases.