期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 74, 期 16, 页码 6035-6041出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo9009497
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资金
- Natural Sciences and Engineering Council of Canada
- Merck-Frosst Canada Ltd.
- Universite de Sherbrooke
We describe the synthesis of (+)-aspidofractinine, the enantiomer of a naturally occurring alkaloid of the kopsane family. Key features of the synthesis include a stereospecific cyanate to isocyanate rearrangement on a chiral scaffold, a ring-closing alkene metathesis to cleave the chiral auxiliary, and a chemoselective cyclopropanation to introduce the quaternary carbon at position 7 of aspidofractinine.
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