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

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.

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anie202016475-s1-mycinolide-iv_si_v3.pdf (Supplementary material), 6MB
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anie202016475-s1-mycinolide-iv_si_v3.pdf
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 Creators:
Herlé, Bart1, Author              
Späth, Georg1, Author              
Schreyer, Lucas1, Author              
Fürstner, Alois1, Author              
Affiliations:
1Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              

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Free keywords: antibiotics; asymmetric hydroformylation; macrolides; redox-isomerization; ruthenium; trans-hydrostannation
 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.

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Language(s): eng - English
 Dates: 2020-12-112021-01-142021-11-152021-03-29
 Publication Status: Published in print
 Pages: 7
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.202016475
 Degree: -

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Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem., Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 60 (14) Sequence Number: - Start / End Page: 7893 - 7899 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851