A general and efficient strategy for 7-aryloctahydroindole and cis-3a-aryloctahydroindole alkaloids: total syntheses of (+/-)-gamma-lycorane and (+/-)-crinane.
A general and efficient approach to both 7-aryloctahydroindole and cis-3a-aryloctahydroindole alkaloids has been developed. The key step involves Michael additions of the corresponding kinetics and thermodynamics lithium enolates of ketone 9 to the versatile building blocks: nitroethylene 10. Two representative members, (+/-)-gamma-lycorane and (+/-)-crinane, have been synthesized in 22 and 36% overall yields, respectively.
Gao
Shuanhu
S
State Key Laboratory of Applied Organic Chemistry and Department of Chemistry, Lanzhou University, Lanzhou 730000, P. R. China.
Tu
Yong Qiang
YQ
Song
Zhenlei
Z
Wang
Aixia
A
Fan
Xiaohui
X
Jiang
Yijun
Y
D047151:Amaryllidaceae Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001685:Biological Factors / Q000138:chemical synthesis / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007700:Kinetics; D008094:Lithium / Q000737:chemistry; D015394:Molecular Structure; D013816:Thermodynamics
D047151:Amaryllidaceae Alkaloids; D001685:Biological Factors; D007211:Indoles; C504763:crinane; C412290:lycorane; D008094:Lithium