Philippine Science Letters
vol. 4 | no. 2 | 2011
published online September 23, 2011


Total synthesis of dubiusamine C, a plausible minor alkaloid in Pandanus dubius

by Mario A. Tan1,2,*, Noriyuki Kogure2, Mariko Kitajima2, Hiromitsu Takayama2

1Research Center for the Natural and Applied Sciences, University of Santo Tomas, Espana, Manila 1015 Philippines
2Graduate School of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522 Japan



Dubiusamine C is a minor alkaloid isolated as a diastereomeric mixture with dubiusamine A. The structure of dubiusamine C was deduced by 1H-NMR analysis and then identified by its racemic total synthesis which employed the Grignard, ring-closing metathesis, stereoselective reduction and Mitsunobu reactions as the key steps, in nine linear steps and an over-all yield of 20%.

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Submitted: July 28, 2011
Revised: September 1, 2011
Accepted: September 5, 2011
Published: September 23, 2011
Editor-in-charge: Fabian M. Dayrit
Fabian M. Dayrit