期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 56, 期 38, 页码 11624-11627出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201706845
关键词
curcusone; diterpenes; gold catalysis; tandem reactions; total synthesis
资金
- NIH [P30CA023168]
- NSF [CHE 1625543]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1625543] Funding Source: National Science Foundation
Total syntheses of the reported structures of the rhamnofolane diterpene natural products curcusones I and J in racemic form were achieved. The synthetic strategy features a novel tandem gold-catalyzed furan formation and furanallene [4+3] cycloaddition to build the 5,7-fused ring system with an oxa-bridge in one step, and a stereoselective exo-Diels-Alder reaction to form the 6-membered ring. The newly developed tandem gold catalysis is quite general and can be scaled up. Our syntheses suggest that structural revisions of curcusones I and J are needed.
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