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Mar. Drugs 2015, 13(8), 4915-4933; doi:10.3390/md13084915

Chemistry of Renieramycins. Part 14: Total Synthesis of Renieramycin I and Practical Synthesis of Cribrostatin 4 (Renieramycin H)

Graduate School of Pharmaceutical Sciences, Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan
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Academic Editor: Orazio Taglialatela-Scafati
Received: 27 June 2015 / Revised: 21 July 2015 / Accepted: 22 July 2015 / Published: 6 August 2015
(This article belongs to the Special Issue Marine Secondary Metabolites)
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Abstract

The first total synthesis of (±)-renieramycin I, which was isolated from the Indian bright blue sponge Haliclona cribricutis, is described. The key step is the selenium oxide oxidation of pentacyclic bis-p-quinone derivative (3) stereo- and regioselectively. We also report a large-scale synthesis of cribrostatin 4 (renieramycin H) via the C3-C4 double bond formation in an early stage based on the Avendaño’s protocol, from readily available 1-acetyl-3-(3-methyl-2,4,5-trimethylphenyl)methyl-piperazine-2,5-dione (8) in 18 steps (8.3% overall yield). The synthesis provides unambiguous evidence supporting the original structure of renieramycin I. View Full-Text
Keywords: cribrostatin 4 (renieramycin H); renieramycin I; total synthesis; structural determination; selenium oxide oxidation; marine natural product cribrostatin 4 (renieramycin H); renieramycin I; total synthesis; structural determination; selenium oxide oxidation; marine natural product
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Yokoya, M.; Kobayashi, K.; Sato, M.; Saito, N. Chemistry of Renieramycins. Part 14: Total Synthesis of Renieramycin I and Practical Synthesis of Cribrostatin 4 (Renieramycin H). Mar. Drugs 2015, 13, 4915-4933.

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