期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 133, 期 50, 页码 20172-20174出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja2098063
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-
资金
- National Institutes of Health, National Institute of General Medical Sciences [R01 GM 090082]
A concise stereoselective total synthesis of (+)-saxitoxin is described. A silver(I)-initiated hydroamination cascade constructs the bicyclic guanidinium ion core from a alkynyl bisguanidine. This sequence creates two C-N bonds, one C-O bond, and three rings and forms a single stereoisomer in a single synthetic transformation. This process enabled us to complete the synthesis of (+)-saxitoxin in 14 steps from N-Boc-L-serine methyl ester.
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