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CC BY-ND-NC 4.0 · SynOpen 2019; 03(04): 148-156
DOI: 10.1055/s-0039-1690336
DOI: 10.1055/s-0039-1690336
paper
Total Synthesis of Bacterial 5-(3-Indolyl)oxazole Alkaloids: Pimprinols A–C
Further Information
Publication History
Received: 16 October 2019
Accepted after revision: 05 November 2019
Publication Date:
28 November 2019 (online)
This paper is dedicated to the memory of Professor József Reiter.
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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690336.
- Supporting Information
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