Total synthesis of the lycopodium alkaloid (+)-serratezomine A.
Total synthesis of the lycopodium alkaloid (+)-serratezomine A.
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DOI：
10.1021/ja900536d
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发表时间：
2009-03-18
影响因子：
15
通讯作者：
Johnston JN
中科院分区：
文献类型：
--
作者：
Chandra A;Pigza JA;Han JS;Mutnick D;Johnston JN
The first total synthesis of (+)-serratezomine A is described. Key aspects of the synthesis include a) the first deployment of free radical-mediated vinyl amination – an intramolecular alkyne aminostannation – in a complex target synthesis, b) the use of a β-stannyl enamine as the lynchpin for convergent assembly of the natural product backbone, c) the use of an oxidative allylation promoted by cerium(IV) (CAN) to establish the all carbon quaternary chiral center with the proper configuration, and d) an intramolecular substitution reaction to form the sensitive bridging lactone. Overall, 15 steps (longest linear sequence) are required to prepare the natural product from a commercially available aldehyde, and assembly of the contiguous array of six stereocenters is accomplished with high stereocontrol.
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影响因子：
16.6
作者：
Evans, DA;Scheerer, JR
通讯作者：
Scheerer, JR
影响因子：
3.6
作者：
Garaas, SD;Hunter, TJ;O'Doherty, GA
通讯作者：
O'Doherty, GA
DOI：
10.1016/s1099-4831(05)61001-2
发表时间：
2005-01-01
期刊：
The Alkaloids. Chemistry and biology
影响因子：
--
作者：
Kobayashi, Jun'ichi;Morita, Hiroshi
通讯作者：
Morita, Hiroshi
影响因子：
15
作者：
Beshore, Douglas C.;Smith, Amos B., III
通讯作者：
Smith, Amos B., III
影响因子：
15
作者：
Bisai, Alakesh;West, Scott P.;Sarpong, Richmond
通讯作者：
Sarpong, Richmond