Frontiers in Chemistry (Nov 2020)

Enantioselective Synthesis of (+)-Coerulescine by a Phase-Transfer Catalytic Allylation of Diphenylmethyl tert-Butyl α-(2-Nitrophenyl)Malonate

  • Sangki Lee,
  • Jewon Yang,
  • Sehun Yang,
  • Geumwoo Lee,
  • Daehyun Oh,
  • Min Woo Ha,
  • Suckchang Hong,
  • Hyeung-geun Park

DOI
https://doi.org/10.3389/fchem.2020.577371
Journal volume & issue
Vol. 8

Abstract

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A 7-step enantioselective synthetic method for preparing (S)(+)-coerulescine is reported through the use of diphenylmethyl tert-butyl α-(2-nitrophenyl)malonate (16% overall yield, >99% ee). Allylation is the key step under phase-transfer catalytic conditions (86% ee). This synthetic method can be used as a practical route for the synthesis of various derivatives of (S)(+)-coerulescine for analyzing its structure–activity relationships against its biological activities.

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