posted on 2017-02-10, 00:00authored byXiangbo Zhao, Wu Li, Junjie Wang, Dawei Ma
The
Hoppe’s homoaldol reaction of a cyclo-hexenyl carbamate
with an aldehyde followed by an unprecedented BF3·OEt2 mediated intramolecular Mukaiyama–Michael-type reaction
affords the tetracyclic core structure of ent-kaurane
diterpenoids. The usage of this convergent approach for assembling
these natural products is demonstrated by the first asymmetric total
syntheses of two highly oxidized ent-kaurane diterpenoids:
Lungshengenin D and 1α,6α-diacetoxy-ent-kaura-9(11),16-dien-12,15-dione.