Total synthesis of norzoanthamine

被引:202
作者
Miyashita, M [1 ]
Sasaki, M [1 ]
Hattori, I [1 ]
Sakai, M [1 ]
Tanino, K [1 ]
机构
[1] Hokkaido Univ, Grad Sch Sci, Div Chem, Sapporo, Hokkaido 0600810, Japan
关键词
D O I
10.1126/science.1098851
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
Norzoanthamine, an alkaloid isolated from Zoanthus sp., can suppress the loss of bone weight and strength in ovariectomized mice. Norzoanthamine derivatives can also strongly inhibit the growth of P-388 murine leukemia cell lines and human platelet aggregation. However, norzoanthamine's densely functionalized complex stereostructure and scarce availability from natural sources have proved a synthetic challenge. We report the stereoselective total synthesis of norzoanthamine in 41 steps, with an overall yield of 3.5% ( an average of 92% yield each step).
引用
收藏
页码:495 / 499
页数:5
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