期刊
CHEMICAL SCIENCE
卷 6, 期 1, 页码 349-353出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c4sc01826e
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资金
- NSF [CHE-1145236]
- NIH [GM 033049]
- John Stauffer Memorial Fellowship
- Stanford Graduate Fellowship
We report a catalytic asymmetric total synthesis of the ascidian natural product perophoramidine. The synthesis employs a molybdenum-catalyzed asymmetric allylic alkylation of an oxindole nucleophile and a monosubstituted allylic electrophile as a key asymmetric step. The enantioenriched oxindole product from this transformation contains vicinal quaternary and tertiary stereocenters, and is obtained in high yield along with high levels of regio-, diastereo-, and enantioselectivity. To install the second quaternary stereocenter in the target, the route utilizes a novel regio- and diastereoselective allylation of a cyclic imino ether to deliver an allylated imino ether product in near quantitative yield and with complete regio- and diastereocontrol. Oxidative cleavage and reductive amination are used as final steps to access the natural product.
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