期刊
TETRAHEDRON
卷 65, 期 33, 页码 6535-6548出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2009.05.060
关键词
Tandem cycloaddition; Nitroalkene; Alkaloid
资金
- NIGMS NIH HHS [R01 GM030938-25, R01 GM030938] Funding Source: Medline
An asymmetric synthesis of the ABCD ring system of daphnilactone B is described. The synthesis features a tandem, double intramolecular, [4+2]/[3+2] cycloaddition of a highly functionalized, enantiomerically enriched nitroalkene to generate a pentacyclic nitroso acetal. The cycloaddition establishes six contiguous stereogenic centers including the critical CID ring junction that bears two quaternary stereogenic centers. Hydrogenolysis of the nitroso acetal followed by amide reduction and cyclization provided the AB rings. The methyl substituent on the A ring was installed in the correct configuration via hydrogenation of an exocyclic olefin in the final step. (C) 2009 Elsevier Ltd. All rights reserved.
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