Total synthesis of (-)-incarvilline, (+)-incarvine C, and (-)-incarvillateine.
The first total syntheses of new monoterpene alkaloids (-)-incarvilline, (+)-incarvine C, and (-)-incarvillateine, corresponding to the natural enantiomers, have been accomplished. The strategy for the synthesis of these natural products utilized 6-epi-incarvilline as a common precursor, which was assembled by a three-component coupling reaction using (4S)-4-siloxy-2-cyclopenten-1-one to construct an appropriately trisubstituted cyclopentanone, followed by ring closure to the cis-perhydro-2-pyrindine skeleton by means of a reductive Heck-type reaction. Furthermore, topochemically controlled [2 + 2] photodimerization of cinnamic acid derivatives in the solid state for the stereospecific construction of a 1,2,3,4-tetrasubstituted cyclobutane ring was also investigated as a means to access (-)-incarvillateine.
Ichikawa
Masaya
M
School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan.
Takahashi
Masaki
M
Aoyagi
Sakae
S
Kibayashi
Chihiro
C
D000470:Alkaloids / Q000138:chemical synthesis*; D003373:Coumaric Acids / Q000737:chemistry; D018360:Crystallography, X-Ray; D019684:Magnoliopsida / Q000737:chemistry; D008958:Models, Molecular; D039821:Monoterpenes / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000470:Alkaloids; D003373:Coumaric Acids; D039821:Monoterpenes; C400141:incarvillateine; C004999:ferulic acid