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  Total Synthesis of Disciformycin A and B: Unusually Exigent Targets of Biological Significance

Kwon, Y., Schulthoff, S., Dao, Q. M., Wirtz, C., & Fürstner, A. (2018). Total Synthesis of Disciformycin A and B: Unusually Exigent Targets of Biological Significance. Chemistry – A European Journal, 24(1), 109-114. doi:10.1002/chem.201705550.

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[369]SI.pdf (Supplementary material), 1002KB
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 Creators:
Kwon, Yonghoon1, Author              
Schulthoff, Saskia1, Author              
Dao, Quang Minh1, 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 metathesis; antibiotics; natural products; protecting groups; total synthesis
 Abstract: The first total synthesis of the potent antibiotic disciformycin B (2) is described, which is exceptionally isomerization-prone and transforms into disciformycin A (1) even under notably mild conditions. To outweigh this bias, the approach to 2 hinged on the use of a silyl residue at C4 to lock the critical double bond in place and hence insure the integrity of the synthetic intermediates en route to 2. This tactic was instrumental for the preparation of the building blocks and formation of the macrocyclic ring via ring closing alkyne metathesis (RCAM). To make the end game successful, however, it proved necessary to cleave the C-silyl protecting group off; it was at this stage that the exceptional sensitivity of the target became fully apparent.

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Language(s): eng - English
 Dates: 2017-11-222017-11-222018-01-02
 Publication Status: Published online
 Pages: 6
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/chem.201705550
 Degree: -

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Title: Chemistry – A European Journal
  Other : Chem. – Eur. J.
  Other : Chem. Eur. J.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 24 (1) Sequence Number: - Start / End Page: 109 - 114 Identifier: ISSN: 0947-6539
CoNE: https://pure.mpg.de/cone/journals/resource/954926979058