Asymmetric total synthesis and X-ray crystal structure of the cytotoxic marine diterpene (+)-vigulariol

被引:44
作者
Becker, Jochen [1 ]
Bergander, Klaus [1 ]
Froehlich, Roland [1 ]
Hoppe, Dieter [1 ]
机构
[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany
关键词
asymmetric synthesis; carbamates; homoaldol reactions; metathesis; total synthesis;
D O I
10.1002/anie.200704678
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Figure Presented) A crystal from the China sea: The asymmetric total synthesis of (+)-vigulariol (see picture: red O, blue C, white H) has been accomplished in eight linear steps starting from (R)-cryptone, which is readily available from eucalyptus oil. Key steps involve an asymmetric homoaldol reaction of chiral allyl carbamates and THF cyclocondensation. Ring-closing metathesis led to the tricyclic framework of the cladiellin diterpenes. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:1654 / 1657
页数:4
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