期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 56, 期 6, 页码 1624-1628出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201611078
关键词
allylation; guaianolides; natural products; terpenes; total synthesis
资金
- NIH [GM116952, S10-RR027172]
- Bristol-Myers Squibb
- Amgen
- UC Berkeley Graduate Division
- National Natural Science Foundation of China [21402149]
- Chinese Scholarship Council (CSC) fellowship program
With over 5000 members isolated to date, sesquiterpene lactones represent a prolific source of medicinal agents with several derivatives in human clinical trials. The guaianolides, a major subset of this group, have been intensely investigated from both medicinal and chemical-synthesis perspectives for decades. To date, the myriad stereochemical permutations presented by this enormous family have precluded the synthesis of many unique members. Herein we report the total synthesis of the trans-fused 8,12-guaianolide (+)-mikanokryptin in 10steps from (+)-carvone. Notably, this synthesis is the first gram-scale total synthesis of a guaianolide natural product.
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