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

Tsuchiya, Satoshi; Sunazuka, Toshiaki; Hirose, Tomoyasu; Mori, Ryuma; Tanaka, Toshiaki; Iwatsuki, Masato; Ōmura, Satoshi

doi:10.1021/ol062282z.s001

ol062282z_si_001.pdf (887.54 kB)

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

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 S_N2 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.