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  Total Synthesis Provides Strong Evidence: Xestocyclamine A is the Enantiomer of Ingenamine

Meng, Z., & Fürstner, A. (2020). Total Synthesis Provides Strong Evidence: Xestocyclamine A is the Enantiomer of Ingenamine. Journal of the American Chemical Society, 142(27), 11703-11708. doi:10.1021/jacs.0c05347.

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ja0c05347_si_001.pdf (Supplementary material), 12MB
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Meng, Zhanchao1, Author              
Fürstner, Alois1, Author              
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1Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              

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 Abstract: Xestocyclamine A ((−)-1) is featured prominently in a biosynthesis pathway leading to a large family of polycyclic alkaloids. The first total synthesis now proves that the structure of this compound had originally been misassigned. The route to (−)-1 is based on a double Michael addition for the formation of the bridged diazadecalin core and a palladium-catalyzed decarboxylative allylation to install the quaternary bridgehead center. Ring-closing alkyne metathesis allowed a 13-membered cycloalkyne to be forged, which was selectively reduced during an involved sequence of hydroboration/selective protodeborylation/alkyl-Suzuki coupling used to close the 11-membered ring. Crystallographic data prove the identity of synthetic (−)-1 with nominal xestocyclamine, but the spectra differ from those of the authentic alkaloid. To clarify the point, the synthesis was redirected toward ingenamine (3), which is supposedly a positional isomer of 1. The recorded data confirm the assignment of this particular natural product and strongly suggest that xestocyclamine A is in fact the enantiomer of ingenamine (+)-3.

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Language(s): eng - English
 Dates: 2020-05-152020-06-162020-07-08
 Publication Status: Published in print
 Pages: 6
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 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/jacs.0c05347
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Title: Journal of the American Chemical Society
  Other : JACS
  Abbreviation : J. Am. Chem. Soc.
Source Genre: Journal
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Publ. Info: Washington, DC : American Chemical Society
Pages: - Volume / Issue: 142 (27) Sequence Number: - Start / End Page: 11703 - 11708 Identifier: ISSN: 0002-7863
CoNE: https://pure.mpg.de/cone/journals/resource/954925376870