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