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Total synthesis of resolvin E2

✍ Scribed by Yusuke Kosaki; Narihito Ogawa; Yuichi Kobayashi

Publisher: Elsevier Science
Year: 2010
Tongue: French
Weight: 589 KB
Volume: 51
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2010.01.109

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✦ Synopsis

Resolvin E2 (2) was synthesized stereoselectively using the C1-8 and C15-20 aldehydes 6 and 9, which were connected to the C9-14 fragment by using Wittig reactions. The aldehyde 6 was prepared from the c-silyl alcohol (S)-20 by a sequence of reactions involving ozonolysis, oxidation with NaIO 4 , and the Wittig reaction of the resulting aldehyde with Ph 3 P@CHCHO, whereas the aldehyde 9 was synthesized from the corresponding c-silyl alcohol through epoxidation, reaction with Et 2 AlCN, and reduction with DIBAL-H.

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