Total Synthesis of Spirastrellolide F Methyl Ester-Part 2: Macrocyclization and Completion of the Synthesis

被引:48
作者
Benson, Stefan [1 ]
Collin, Marie-Pierre [1 ]
O'Neil, Gregory W. [1 ]
Ceccon, Julien [1 ]
Fasching, Bernhard [1 ]
Fenster, Michael D. B. [1 ]
Godbout, Cedrickx [1 ]
Radkowski, Karin [1 ]
Goddard, Richard [1 ]
Fuerstner, Alois [1 ]
机构
[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
关键词
cross-coupling; hydrogenation; macrolides; natural products; total synthesis; NATURAL-PRODUCT SYNTHESIS; DEF-BIS-SPIROACETAL; STRUCTURE ELUCIDATION; AMPHIDINOLIDE-X; A CONSTRUCTION; FRAGMENT; SUBUNIT; TRIOXADISPIROKETAL; CONFIGURATION; DERIVATIVES;
D O I
10.1002/anie.200906122
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(figure represented) Marvel of the sea: A concise and highly convergent total synthesis of the methyl ester of the marine macrolide spirastrellolide F (see picture), which has exquisite antimitotic properties, is reported. In this approach, the northern and the southern hemispheres of this intricate target are stitched together in only two consecutive steps (Suzuki coupling, Yamaguchi lactonization) without any interim protectinggroup manipulations. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:9946 / 9950
页数:5
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