Construction of Successive Stereogenic Centers of ent -Kauranoid through an Oxidative Dearomatization/1,2-Shift Cascade

Yuki Imamura, Hikaru Mizutani, Masahisa Nakada*

*この研究の対応する著者

研究成果: Article査読

抄録

The construction of the successive stereogenic centers, including an all-carbon quaternary stereogenic center, of ent-kauranoid through an oxidative dearomatization/1,2-shift cascade is described. The developed cascade reaction of a substrate bearing a trans-2-(p-methoxyphenyl) vinyl group as the migrating group afforded the desired product in 83% yield. The 1,2-shift in the cascade is strongly affected by a stereoelectronic effect. The X-ray crystal structure of a compound bearing four successive stereogenic centers in the fused-ring moiety of ent-kauranoid diterpene, which was prepared by the oxidative dearomatization/1,2-shift cascade and subsequent stereoselective transformations, is also reported.

本文言語English
ページ(範囲)1556-1562
ページ数7
ジャーナルSynlett
33
15
DOI
出版ステータスPublished - 2022 8月 29

ASJC Scopus subject areas

  • 有機化学

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