期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 53, 期 35, 页码 9257-9261出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201404499
关键词
boron; cyclization; natural products; synthetic methods; total synthesis
资金
- National High Technology Projects 973 [2012CB837400]
- NNSFC [21222209, 91313303]
- National Institute of General Medical Sciences [GM 094478]
The first enantioselective total syntheses of prenylflavonoid Diels Alder natural products (-)-kuwanon (-)-kuwanon J, (-)-brosimone A, and (-)-brosimone B have been accomplished from a common intermediate based on a concise synthetic strategy. Key elements of the synthesis include a biosynthesis-inspired asymmetric Diels Alder cyclo-addition mediated by a chiral ligand/boron Lewis acid, as well as a process involving regioselective Schenck ene reaction, reduction, and dehydration to realize a biomimetic dehydrogenation for generation of the required diene precursor. Furthermore, a remarkable tandem interlintramolecular asymmetric Diels Alder cycloaddition process was applied for the synthesis of (-)-brosimone A.
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