α- and β-Lipomycin : total syntheses by sequential stille couplings and assignment of the absolute configuration of all stereogenic centers
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim..
40 years ago spectroscopy, derivatization, and degradation revealed the structures of α-lipomycin and its aglycon β-lipomycin except for the configurations of their side-chain stereocenters. We synthesized all relevant β-lipomycin candidates: the (12R,13S) isomer has the same specific rotational value as the natural product. By the same criterion the (12R,13S)-configured D-digitoxide is identical to α-lipomycin. We double-checked our assignments by degrading α- and β-lipomycin to the diesters 33 and 34 and proving their 3D structures synthetically.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2014 |
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| Erschienen: |
2014 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:53 |
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| Enthalten in: |
Angewandte Chemie (International ed. in English) - 53(2014), 28 vom: 07. Juli, Seite 7328-34 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Hofferberth, Max L [VerfasserIn] |
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| Links: |
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| Themen: |
Configuration determination |
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| Anmerkungen: |
Date Completed 21.05.2015 Date Revised 03.07.2014 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1002/anie.201402255 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM238857050 |
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| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. | ||
| 520 | |a 40 years ago spectroscopy, derivatization, and degradation revealed the structures of α-lipomycin and its aglycon β-lipomycin except for the configurations of their side-chain stereocenters. We synthesized all relevant β-lipomycin candidates: the (12R,13S) isomer has the same specific rotational value as the natural product. By the same criterion the (12R,13S)-configured D-digitoxide is identical to α-lipomycin. We double-checked our assignments by degrading α- and β-lipomycin to the diesters 33 and 34 and proving their 3D structures synthetically | ||
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