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A Convergent Synthesis of Gonytolide C Using an Intramolecular Oxa‐Michael Addition
Author(s) -
Li Freda F.,
Atkinson Darcy J.,
Furkert Daniel P.,
Brimble Margaret A.
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501402
Subject(s) - michael reaction , intramolecular force , chemistry , natural product , convergent synthesis , total synthesis , stereochemistry , combinatorial chemistry , organic chemistry , catalysis
A full account of the evolution of a convergent total synthesis of gonytolide C is reported. The assembly of the natural product core relies on a Horner–Wadsworth–Emmons (HWE) olefination followed by an intramolecular oxa‐Michael addition. Robust and efficient preparations of both HWE coupling partners were established. The synthesis enabled further investigation of an asymmetric oxa‐Michael cyclisation to prepare gonytolide C, demonstrating the utility of this strategy for synthesis of 2,2‐disubstituted chromanones.