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A High‐Yielding Modular Access to the Lamellarins: Synthesis of Lamellarin G Trimethyl Ether, Lamellarin η and Dihydrolamellarin η
Author(s) -
Imbri Dennis,
Tauber Johannes,
Opatz Till
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201303563
Subject(s) - aldehyde , pyrrole , ring (chemistry) , ether , stereochemistry , modular design , chemistry , organic chemistry , computer science , catalysis , operating system
A deprotonated α‐aminonitrile serves as a key intermediate in a highly efficient (95 % per step on average; see scheme) modular synthetic approach to the lamellarin alkaloids. Its reaction with an α,β‐unsaturated aldehyde forms the central pyrrole ring in a one‐pot procedure. The construction of the fused pentacyclic skeleton is completed by a microwave‐assisted Ullmann‐type lactone formation.