Total Synthesis of (+)-Daphmanidin E

被引:152
作者
Weiss, Matthias E. [1 ]
Carreira, Erick M. [1 ]
机构
[1] ETH, Organ Chem Lab, CH-8093 Zurich, Switzerland
关键词
alkaloids; C-C coupling; cyclization; natural products; total synthesis; ASYMMETRIC CONJUGATE ADDITIONS; NATURAL PRODUCT SYNTHESIS; RADICAL REACTIONS; ORGANIC-SYNTHESIS; CYCLIZATION; ACID; CHEMISTRY; NITROALKENES; DERIVATIVES; ALKALOIDS;
D O I
10.1002/anie.201104681
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
From ring to ring: The first total synthesis of (+)-daphmanidinE features rapid access to an enantiomerically pure bicyclo[2.2.2]octadione and elaboration around its periphery through the implementation of two Claisen rearrangements, the use of a copper/peptide complex for reagent-controlled stereoselective conjugate addition, a diastereoselective hydroboration, and a cobalt-catalyzed alkyl-Heck cyclization. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:11501 / 11505
页数:5
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