Total Synthesis of Bacterial 5-(3-Indolyl)oxazole Alkaloids: Pimprinols A–C
Abstract Pimprinols A, B, and C are bacterial 5-(3-indolyl)oxazole alkaloids that have been isolated from Streptomyces sp. Lv3–13. In this paper, we report a new synthesis of pimprinol A and the first total synthesis of pimprinol B and pimprinol C. In addition, antipodes of the naturally occurring p...
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| Format: | Article |
| Language: | English |
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Georg Thieme Verlag KG
2019-10-01
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| Series: | SynOpen |
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| Online Access: | http://www.thieme-connect.de/DOI/DOI?10.1055/s-0039-1690336 |
| _version_ | 1828928099951050752 |
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| author | Tímea Szabó Róbert Kormány András Dancsó Balázs Volk Mátyás Milen |
| author_facet | Tímea Szabó Róbert Kormány András Dancsó Balázs Volk Mátyás Milen |
| author_sort | Tímea Szabó |
| collection | DOAJ |
| description | Abstract
Pimprinols A, B, and C are bacterial 5-(3-indolyl)oxazole alkaloids that have been isolated from Streptomyces sp. Lv3–13. In this paper, we report a new synthesis of pimprinol A and the first total synthesis of pimprinol B and pimprinol C. In addition, antipodes of the naturally occurring pimprinols A and C, as well as the racemates of these two alkaloids were also prepared. In the pivotal step, the 1,3-oxazole ring was constructed by a Nicolaou’s modified Robinson–Gabriel cyclization. |
| first_indexed | 2024-12-13T23:59:30Z |
| format | Article |
| id | doaj.art-0ab34f6a291b4ed4be5665c811a94886 |
| institution | Directory Open Access Journal |
| issn | 2509-9396 |
| language | English |
| last_indexed | 2024-12-13T23:59:30Z |
| publishDate | 2019-10-01 |
| publisher | Georg Thieme Verlag KG |
| record_format | Article |
| series | SynOpen |
| spelling | doaj.art-0ab34f6a291b4ed4be5665c811a948862022-12-21T23:26:23ZengGeorg Thieme Verlag KGSynOpen2509-93962019-10-01030414815610.1055/s-0039-1690336Total Synthesis of Bacterial 5-(3-Indolyl)oxazole Alkaloids: Pimprinols A–CTímea SzabóRóbert KormányAndrás DancsóBalázs VolkMátyás MilenAbstract Pimprinols A, B, and C are bacterial 5-(3-indolyl)oxazole alkaloids that have been isolated from Streptomyces sp. Lv3–13. In this paper, we report a new synthesis of pimprinol A and the first total synthesis of pimprinol B and pimprinol C. In addition, antipodes of the naturally occurring pimprinols A and C, as well as the racemates of these two alkaloids were also prepared. In the pivotal step, the 1,3-oxazole ring was constructed by a Nicolaou’s modified Robinson–Gabriel cyclization.http://www.thieme-connect.de/DOI/DOI?10.1055/s-0039-1690336oxazolenatural productsbacterial alkaloidspimprinols a–ctotal synthesis |
| spellingShingle | Tímea Szabó Róbert Kormány András Dancsó Balázs Volk Mátyás Milen Total Synthesis of Bacterial 5-(3-Indolyl)oxazole Alkaloids: Pimprinols A–C SynOpen oxazole natural products bacterial alkaloids pimprinols a–c total synthesis |
| title | Total Synthesis of Bacterial 5-(3-Indolyl)oxazole Alkaloids: Pimprinols A–C |
| title_full | Total Synthesis of Bacterial 5-(3-Indolyl)oxazole Alkaloids: Pimprinols A–C |
| title_fullStr | Total Synthesis of Bacterial 5-(3-Indolyl)oxazole Alkaloids: Pimprinols A–C |
| title_full_unstemmed | Total Synthesis of Bacterial 5-(3-Indolyl)oxazole Alkaloids: Pimprinols A–C |
| title_short | Total Synthesis of Bacterial 5-(3-Indolyl)oxazole Alkaloids: Pimprinols A–C |
| title_sort | total synthesis of bacterial 5 3 indolyl oxazole alkaloids pimprinols a c |
| topic | oxazole natural products bacterial alkaloids pimprinols a–c total synthesis |
| url | http://www.thieme-connect.de/DOI/DOI?10.1055/s-0039-1690336 |
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