期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 132, 期 40, 页码 14064-14066出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja107141p
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资金
- Fonds der Chemischen Industrie
- MPG
An efficient total synthesis of the antiproliferative macrolide and cell migration inhibitor lactimidomycin (3) is reported, which relies on the performance of ring closing alkyne metathesis (RCAM). The strained 12-membered 1,3-enyne 21 as the key intermediate was forged with the aid of [(Ph3SiO)(3)Mo equivalent to CPh]center dot OEt2 (27) as the most effective member of a new generation of powerful alkyne metathesis catalysts. 21 was elaborated to the target by a ruthenium catalyzed trans-hydrosilylation/proto-desilylation sequence and a highly diastereoselective Mukaiyama aldol reaction controlled by oxazaborolidinone 29 as strategic operations.
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