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Collective Total Synthesis of Aspidofractinine Alkaloids through the Development of a Bischler-Napieralski/Semipinacol Rearrangement Reaction.

Authors :
Wang SH
Si RQ
Zhuang QB
Guo X
Ke T
Zhang XM
Zhang FM
Tu YQ
Source :
Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2020 Dec 01; Vol. 59 (49), pp. 21954-21958. Date of Electronic Publication: 2020 Sep 29.
Publication Year :
2020

Abstract

A tandem Bischler-Napieralski/semipinacol rearrangement reaction has been developed for the purpose of assembling a bis(spirocyclic) indole framework, a privileged structural unit of aspidofractinine-type monoterpenoid indole alkaloids, and was used in combination with a subsequent Mannich reaction to expeditiously construct the central bridged bicyclo[2.2.1]heptane ring system of these molecules with contiguous quaternary centers. The development of this novel strategy culminated in the collective total synthesis of four aspidofractinine alkaloids.<br /> (© 2020 Wiley-VCH GmbH.)

Details

Language :
English
ISSN :
1521-3773
Volume :
59
Issue :
49
Database :
MEDLINE
Journal :
Angewandte Chemie (International ed. in English)
Publication Type :
Academic Journal
Accession number :
32851781
Full Text :
https://doi.org/10.1002/anie.202009238