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Synlett 2018; 29(05): 609-612
DOI: 10.1055/s-0036-1591739
DOI: 10.1055/s-0036-1591739
letter
A Combined Tamaru Allylation/Olefin Cross-Metathesis Approach for the Total Syntheses of (±)-Paniculidine B, (±)-Paniculidine C, and 2-Methylcarbazole
We thank the Ministry of Science and Technology, Taiwan for financial support of this work (Grant Nos. 104-2113-M-009-022-MY2 and 106-2113-M-009-011-MY2).Further Information
Publication History
Received: 07 October 2017
Accepted after revision: 18 November 2017
Publication Date:
20 December 2017 (online)
Abstract
A concise approach to the total syntheses of racemic paniculidines B and C is described. The route features a combined Tamaru allylation/olefin cross-metathesis sequence for the regiocontrolled synthesis of prenylindole intermediates. In addition, we report a transformation of the prenylated indole into 2-methylcarbazole catalyzed by sulfonic acid-functionalized silica gel.
Key words
prenylindoles - Tamaru allylation - cross-metathesis - carbazoles - total synthesis - alkaloidsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591739.
- Supporting Information
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References and Notes
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For a comprehensive review on carbazole alkaloids, see:
For leading examples, see:
For conceptually relevant examples, see:
β-Hydroxysulfonic acid-functionalized silica gel (HO-SAS; Chromatorex-DPR, 0.5 mmol/g of SO3H) has been commercially developed by Fuji Silysia Chemical Ltd. For applications of HO-SAS as a catalyst in organic synthesis, see: