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

Marine Drugs

Masashi Yokoya²  Keiichiro Kobayashi²  Mitsuhiro Sato²  Naoki Saito¹ 

[1] Graduate School of Pharmaceutical Sciences, Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan;

关键词: cribrostatin 4 (renieramycin H);    renieramycin I;    total synthesis;    structural determination;    selenium oxide oxidation;    marine natural product;   

DOI  :  10.3390/md13084915

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2015 by the authors; licensee MDPI, Basel, Switzerland.