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.

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Alkaloids U 0600Total Synthesis of (-)-Incarvilline. -(ICHIKAWA, M.; AOYAGI, S.; KIBAYASHI*, C.; Tetrahedron Lett. 46 (2005) 13, 2327-2329; Sch. Pharm., Tokyo Univ. Pharm. Life Sci., Hachioji, Tokyo 192-03, Japan; Eng.) -Mais 30-179

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