TY - JOUR
T1 - Enantioselective synthesis of aurisides A and B, cytotoxic macrolide glycosides of marine origin
AU - Suenaga, Kiyotake
AU - Hoshino, Hiroshi
AU - Yoshii, Takanori
AU - Mori, Kazunori
AU - Sone, Hiroki
AU - Bessho, Yuhki
AU - Sakakura, Akira
AU - Hayakawa, Ichiro
AU - Yamada, Kiyoyuki
AU - Kigoshi, Hideo
N1 - Funding Information:
This study was supported in part by the 21st Century COE program and Grants-in-Aid for Scientific Research from Ministry of Education, Culture, Sports, Science and Technology, Suntory Institute for Bioorganic Research, Yamada Science Foundation, Astellas Foundation for Research on Medicinal Resources, the Naito Foundation, Shorai Foundation for Science and Technology, University of Tsukuba Research Projects, and Wako Pure Chemical Industries, Ltd. We are grateful to Daiso Co., Ltd for donation of chiral trityl glycidyl ether. The IR spectra and optical rotations were recorded at Chemical Analysis Center, University of Tsukuba.
PY - 2006/8/14
Y1 - 2006/8/14
N2 - The enantioselective synthesis of aurisides A and B, macrolide glycosides of marine origin, was achieved by a convergent approach. The C1-C9 segment 4 was prepared from (R)-pantolactone, and the C10-C17 segment 14 was synthesized from (R)-glycidyl trityl ether. The Nozaki-Hiyama-Kishi reaction between 4 and 14 and subsequent reactions gave seco acid 10, which was converted into the aglycon (3) of aurisides by construction of the 14-membered lactone and bromine-substituted conjugated diene. The glycosylation reaction of the aglycon provided aurisides A and B.
AB - The enantioselective synthesis of aurisides A and B, macrolide glycosides of marine origin, was achieved by a convergent approach. The C1-C9 segment 4 was prepared from (R)-pantolactone, and the C10-C17 segment 14 was synthesized from (R)-glycidyl trityl ether. The Nozaki-Hiyama-Kishi reaction between 4 and 14 and subsequent reactions gave seco acid 10, which was converted into the aglycon (3) of aurisides by construction of the 14-membered lactone and bromine-substituted conjugated diene. The glycosylation reaction of the aglycon provided aurisides A and B.
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U2 - 10.1016/j.tet.2006.05.077
DO - 10.1016/j.tet.2006.05.077
M3 - Article
AN - SCOPUS:33745608429
SN - 0040-4020
VL - 62
SP - 7687
EP - 7698
JO - Tetrahedron
JF - Tetrahedron
IS - 33
ER -
