American Chemical Society
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Asymmetric Total Synthesis of (+)-K01-0509 B:  Determination of Absolute Configuration

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journal contribution
posted on 2006-11-23, 00:00 authored by Satoshi Tsuchiya, Toshiaki Sunazuka, Tomoyasu Hirose, Ryuma Mori, Toshiaki Tanaka, Masato Iwatsuki, Satoshi Ōmura
K01-0509 B is a novel natural product which contains a carbamoylated cyclic guanidine. Our asymmetric total synthesis features a Sharpless asymmetric epoxidation and a stereocontrolled construction of the cyclic guanidine via an asymmetric nitroaldol reaction, followed by intramolecular SN2 cyclization. These reactions allowed the cyclic guanidine and the adjacent hydroxy group to be assembled, facilitating the asymmetric total synthesis and determination of the absolute stereochemistry of K01-0509 B.