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  Collective Total Synthesis of Casbane Diterpenes: One Strategy, Multiple Targets

Löffler, L. E., Wirtz, C., & Fürstner, A. (2021). Collective Total Synthesis of Casbane Diterpenes: One Strategy, Multiple Targets. Angewandte Chemie International Edition, 60(10), 5316-5322. doi:10.1002/anie.202015243.

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anie202015243-s1-casbane_diterpenoids_si_v5.pdf (Supplementary material), 7MB
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anie202015243-s1-casbane_diterpenoids_si_v5.pdf
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 Creators:
Löffler, Lorenz E.1, Author              
Wirtz, Conny2, Author              
Fürstner, Alois1, Author              
Affiliations:
1Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              
2Service Department Farès (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445623              

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Free keywords: alkyne methathesis; cyclopropanes; hydrostannation; macrocycles; terpenes
 Abstract: Of the more than 100 casbane diterpenes known to date, only the eponymous parent hydrocarbon casbene itself has ever been targeted by chemical synthesis. Outlined herein is a conceptually new approach that brings not a single but a variety of casbane derivatives into reach, especially the more highly oxygenated and arguably more relevant members of this family. The key design elements are a catalyst‐controlled intramolecular cyclopropanation with or without subsequent equilibration, chain extension of the resulting stereoisomeric cyclopropane building blocks by chemoselective hydroboration/cross‐coupling, and the efficient closure of the strained macrobicyclic framework by ring‐closing alkyne metathesis. A hydroxy‐directed catalytic trans‐hydrostannation allows for late‐stage diversity. These virtues are manifested in the concise total syntheses of depressin, yuexiandajisu A, and ent‐pekinenin C. The last compound turned out to be identical to euphorhylonal A, the structure of which had clearly been misassigned.

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Language(s): eng - English
 Dates: 2020-11-152020-12-082021-03-01
 Publication Status: Published in print
 Pages: 7
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.202015243
 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 (10) Sequence Number: - Start / End Page: 5316 - 5322 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851