A1 Journal article (refereed)
Total Synthesis of Stemoamide, 9a-epi-Stemoamide, and 9a,10-epi-Stemoamide: Divergent Stereochemistry of the Final Methylation Steps (2020)


Siitonen, Juha H.; Csókás, Dániel; Pápai, Imre; Pihko, Petri M. (2020). Total Synthesis of Stemoamide, 9a-epi-Stemoamide, and 9a,10-epi-Stemoamide: Divergent Stereochemistry of the Final Methylation Steps. Synlett, 31 (16), 1581-1586. DOI: 10.1055/s-0040-1707201


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Publication details

All authors or editors: Siitonen, Juha H.; Csókás, Dániel; Pápai, Imre; Pihko, Petri M.

Journal or series: Synlett

ISSN: 0936-5214

eISSN: 1437-2096

Publication year: 2020

Volume: 31

Issue number: 16

Pages range: 1581-1586

Publisher: Georg Thieme Verlag KG

Publication country: Germany

Publication language: English

DOI: http://doi.org/10.1055/s-0040-1707201

Open Access: Publication channel is not openly available


Abstract

Total syntheses of stemoamide, 9a-epi-stemoamide, and 9a,10-epi-stemoamide by a convergent A + B ring-forming strategy is reported. The synthesis required a diastereoselective late-stage methylation of the ABC stemoamide core that successfully enabled access to three of the four possible diastereomeric structures. For the natural stemoamide series, the diastereoselectivity can be rationalized both by kinetic and thermodynamic arguments, whereas for the natural 9a-epi-stemoamide series, the kinetic selectivity is explained by the prepyramidalization of the relevant enolate.


Keywords: chemical synthesis; alkaloids

Free keywords: total synthesis; Stemona alkaloids; cyclic stereocontrol; Mukaiyama-Michael reaction; DFT calculation


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Preliminary JUFO rating: 1


Last updated on 2020-18-09 at 07:11