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Total Synthesis of Mycinolide IV and Path‐Scouting for Aldgamycin N

MPS-Authors
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Herlé,  Bart
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Späth,  Georg
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Schreyer,  Lucas
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Fürstner,  Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Supplementary Material (public)

anie202016475-s1-mycinolide-iv_si_v3.pdf
(Supplementary material), 6MB

Citation

Herlé, B., Späth, G., Schreyer, L., & Fürstner, A. (2021). Total Synthesis of Mycinolide IV and Path‐Scouting for Aldgamycin N. Angewandte Chemie International Edition, 60(14), 7893-7899. doi:10.1002/anie.202016475.


Cite as: http://hdl.handle.net/21.11116/0000-0008-4BA5-A
Abstract
Proof‐of‐concept is provided that a large estate of 16‐membered macrolide antibiotics can be reached by a “unified” approach. The key building block was formed on scale by an asymmetric vinylogous Mukaiyama aldol reaction; its alkene terminus was then converted either into the corresponding methyl ketone by Wacker oxidation or into a chain‐extended aldehyde by catalyst‐controlled branch‐selective asymmetric hydroformylation. These transformations ultimately opened access to two structurally distinct series of macrolide targets. Notable late‐stage maneuvers comprise a rare example of a ruthenium‐catalyzed redox isomerization of an 1,3‐enyne‐5‐ol into a 1,3‐diene‐5‐one derivative, as well as the elaboration of a tertiary propargylic alcohol into an acyloin by trans‐hydrostannation/Chan‐Lam‐type coupling. Moreover, this case study illustrates the underutilized possibility of forging complex macrolactone rings by transesterification under essentially neutral conditions.