Premium
An Approach towards the Synthesis of the Spiroimine Fragment of 13‐Desmethylspirolide C and Gymnodimine A
Author(s) -
Guthertz Alexandre,
Lusseau Jonathan,
Desvergnes Valérie,
Massip Stéphane,
Landais Yannick
Publication year - 2019
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.201804972
Subject(s) - stereocenter , fragment (logic) , alkylation , stereochemistry , yield (engineering) , wittig reaction , chemistry , quaternary carbon , sequence (biology) , organic chemistry , mathematics , enantioselective synthesis , catalysis , algorithm , physics , biochemistry , thermodynamics
Abstract A general access to the spiroimine skeleton of gymnodimine and spirolides is described, relying on the construction of the cyclohexene fragment using an enantiocontrolled Diels–Alder reaction, the installation of the all‐carbon quaternary stereocenter through a stereocontrolled alkylation or aldolisation and the elaboration of the lateral chains at C7 and C22 using Wittig–Horner olefinations. The spiroimine core of gymnodimine is made available through a 16‐step linear sequence in a 21 % overall yield.