ol7b02610_si_002.cif (18.14 kB)
Tunable Cyclization Strategy for the Synthesis of Zizaene-, allo-Cedrane-, seco-Kaurane-, and seco-Atesane-Type Skeletons
dataset
posted on 2017-09-20, 22:14 authored by Qianqian Yang, Wenjing Ma, Gaopeng Wang, Wenli Bao, Xiaoshu Dong, Xuefeng Liang, Lizhi Zhu, Chi-Sing LeeA versatile Lewis
acid-mediated cyclization strategy has been developed
for selectively establishing zizaene-, allo-cedrane-, seco-kaurane-, and seco-atesane-type skeletons.
The zizaene- and seco-atesane-type skeletons can
be obtained in a cascade manner, which involves Diels–Alder
reaction of cyclic enones with bis-silyloxy dienes and carbocyclization
of yne–enolates through Lewis acid dependent 5- or 6-exo-dig modes. This cyclization strategy was also employed
for the core synthesis of tashironin.