Development of the Claisen Rearrangement/Organocatalytic Diels-Alder Approach for the Synthesis of Eunicellins*

Joel F. Hooper; Jonathan M. White; Andrew B. Holmes

doi:10.1071/CH14030

RESEARCH ARTICLE

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Development of the Claisen Rearrangement/Organocatalytic Diels-Alder Approach for the Synthesis of Eunicellins*

Joel F. Hooper ^A ^B , Jonathan M. White ^A and Andrew B. Holmes ^A

+ Author Affiliations

- Author Affiliations

^A School of Chemistry, Bio21 Institute, The University of Melbourne, 30 Flemington Rd, Parkville, Victoria 3010, Australia.

^B Corresponding author. Email: joel.hooper@unimelb.edu.au

Australian Journal of Chemistry 67(9) 1189-1194 https://doi.org/10.1071/CH14030
Submitted: 22 January 2014 Accepted: 1 March 2014 Published: 12 May 2014

Abstract

The intramolecular Diels-Alder approach to synthesizing eunicellins has proved to be a powerful method for the synthesis of this class of natural products. The key to the success of this strategy is control over the endo/exo selectivity of the cycloaddition reaction, which we have addressed through an organocatalytic reaction employing the MacMillan imidazolidinone catalyst. This approach has been further developed to address the issue of functionality at the C8 position, and a novel scalable method for the extension of the medium-ring lactone has been developed.

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[25] Space group P2(1)2(1)2(1); unit cell dimensions a = 5.2539(3) Å, b = 17.363(2) Å, c = 25.103(3) Å; α = 90°; β = 90°; γ = 90°; V = 2290.0(4) Å³; Z = 4; D = 1.231 mg m^–3; F(000) = 920; molecular formula = C₂₇H₃₆O₄; M_w = 424.5723.

Development of the Claisen Rearrangement/Organocatalytic Diels-Alder Approach for the Synthesis of Eunicellins*

Abstract

References

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