title: A general and efficient strategy for 7-aryloctahydroindole and cis-3a-aryloctahydroindole alkaloids: total syntheses of (+/-)-gamma-lycorane and (+/-)-crinane.
abstract: 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.
authors.affiliation: State Key Laboratory of Applied Organic Chemistry and Department of Chemistry, Lanzhou University, Lanzhou 730000, P. R. China.
authors.forename: Shuanhu
authors.initials: S
authors.lastname: Gao
authors.forename: Yong Qiang
authors.initials: YQ
authors.lastname: Tu
authors.forename: Zhenlei
authors.initials: Z
authors.lastname: Song
authors.forename: Aixia
authors.initials: A
authors.lastname: Wang
authors.forename: Xiaohui
authors.initials: X
authors.lastname: Fan
authors.forename: Yijun
authors.initials: Y
authors.lastname: Jiang
mesh_terms: 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
chemical_list: D047151:Amaryllidaceae Alkaloids; D001685:Biological Factors; D007211:Indoles; C504763:crinane; C412290:lycorane; D008094:Lithium