Display options
Cite
von Drathen T, Hoffmann F, Brasholz M. Visible-Light Catalytic Photooxygenation of Monoterpene Indole Alkaloids: Access to Spirooxindole-1,3-oxazines. Chemistry. 2018;doi: 10.1002/chem.201801882.
von Drathen, T., Hoffmann, F., & Brasholz, M. (2018). Visible-Light Catalytic Photooxygenation of Monoterpene Indole Alkaloids: Access to Spirooxindole-1,3-oxazines. Chemistry (Weinheim an der Bergstrasse, Germany), . https://doi.org/10.1002/chem.201801882
von Drathen, Thorsten, et al. "Visible-Light Catalytic Photooxygenation of Monoterpene Indole Alkaloids: Access to Spirooxindole-1,3-oxazines." Chemistry (Weinheim an der Bergstrasse, Germany) vol. (2018). doi: https://doi.org/10.1002/chem.201801882
von Drathen T, Hoffmann F, Brasholz M. Visible-Light Catalytic Photooxygenation of Monoterpene Indole Alkaloids: Access to Spirooxindole-1,3-oxazines. Chemistry. 2018 May 11; doi: 10.1002/chem.201801882. Epub 2018 May 11. PMID: 29750377.
Copy Download .nbib Format: NLM
Share it on

Chemistry. 2018 May 11; doi: 10.1002/chem.201801882. Epub 2018 May 11.

Visible-Light Catalytic Photooxygenation of Monoterpene Indole Alkaloids: Access to Spirooxindole-1,3-oxazines.

Chemistry (Weinheim an der Bergstrasse, Germany)

Thorsten von Drathen, Frank Hoffmann, Malte Brasholz

Affiliations

  1. Department of Chemistry, Institute of Organic Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, 20146, Hamburg, Germany.
  2. Department of Chemistry, Institute of Inorganic Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, 20146, Hamburg, Germany.
  3. Institute of Chemistry-Organic Chemistry, University of Rostock, Albert-Einstein-Str. 3A, 18059, Rostock, Germany.

PMID: 29750377 DOI: 10.1002/chem.201801882

Abstract

Few natural oxindole alkaloids possess an exceptional spiro-[(1,3)oxazinan-3,6'-oxindole] core structure, which results from an unusual oxidative indole rearrangement. The Rauvolfia alkaloid reserpine can be converted into the spirooxindole-1,3-oxazines dioxyreserpine and trioxyreserpine through efficient visible-light catalytic photooxygenation with anthraquinone photocatalysts. A mechanistic investigation sheds new light on the photooxidative rearrangement of reserpine and related monoterpene indole alkaloids, and the spirooxindole-1,3-oxazine products can be valorized by reductive ring opening, to obtain cis-decahydroisoquinolines as new enantiopure synthetic building blocks, as demonstrated for dioxyreserpine.

© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: alkaloids; photochemistry; reaction mechanisms; rearrangement; spiro compounds

Publication Types