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Communication | Special issue | Vol 77, No. 2, 2009, pp.855-863
Published online, 11th November, 2008
DOI: 10.3987/COM-08-S(F)120
Flexible Access to Monoterpenoid Indole Alkaloids Using a Cyclopentanoid Chiral Building Block

Masato Hayashi, Keiichi Motosawa, Atsushi Satoh, Masatoshi Shibuya, Kunio Ogasawara, and Yoshiharu Iwabuchi*

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan


Expedient, diasterocontrolled transformations of 1 to the key synthetic intermediate of corynanthe, iboga, and aspidosperma-class of monoterpenoid indole alkaloids which led up to a formal synthesis of (+)-20R-dihydrocleavamine, (–)-eburnamonine, and a total synthesis of (+)-aspidospermidine (2) have been demonstrated.