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. 2019 Apr 5;21(7):2421-2425.
doi: 10.1021/acs.orglett.9b00722. Epub 2019 Mar 22.

Synthesis of a Diastereomer of the Marine Macrolide Lytophilippine A

André Klüppel  1 , Annika Gille  1 , Ceren Ester Karayel  1 , Martin Hiersemann  1
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Synthesis of a Diastereomer of the Marine Macrolide Lytophilippine A

André Klüppel et al. Org Lett. .

Abstract

The synthesis of a diastereomer of lytophilippine A required 22 longest linear steps using known building blocks. Cross-metathesis/asymmetric aldol addition and regioselective esterification/ring-closing metathesis served as efficient combi tools for scaffold construction. Detailed NMR investigations in different solvent (systems) provide evidence for a deep-seated configurational misassignment of the molecule named lytophilippine A.

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