A catalytic asymmetric total synthesis of (-)-perophoramidine

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Trost, B. M.; Osipov, M.; Krueger, S.; Zhang, Y.: A catalytic asymmetric total synthesis of (-)-perophoramidine. In: Chemical Science 6 (2015), Nr. 1, S. 349-353. DOI: http://dx.doi.org/10.1039/c4sc01826e

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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.
License of this version: CC BY-NC 3.0
Document Type: article
Publishing status: publishedVersion
Issue Date: 2014-07-30
Appears in Collections:Naturwissenschaftliche Fakultät

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pos. country downloads
total perc.
1 image of flag of Germany Germany 98 85.22%
2 image of flag of United States United States 3 2.61%
3 image of flag of Poland Poland 3 2.61%
4 image of flag of Taiwan Taiwan 2 1.74%
5 image of flag of Vietnam Vietnam 1 0.87%
6 image of flag of No geo information available No geo information available 1 0.87%
7 image of flag of Netherlands Netherlands 1 0.87%
8 image of flag of Korea, Republic of Korea, Republic of 1 0.87%
9 image of flag of Kenya Kenya 1 0.87%
10 image of flag of Brazil Brazil 1 0.87%
    other countries 3 2.61%

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