𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Total synthesis of resolvin E1

✍ Scribed by Narihito Ogawa; Yuichi Kobayashi

Publisher
Elsevier Science
Year
2009
Tongue
French
Weight
489 KB
Volume
50
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

Resolvin E1 (RvE1), which is an endogenous mediator to resolve inflammation, was synthesized by Wittig reaction between the C15-C20 aldehyde and the C10-C14 phosphonium salt possessing the vinyl iodo moiety followed by Suzuki-Miyaura coupling of the resulting vinyl iodide with the vinyl borane of the C1-C9 part, which was derived from the corresponding acetylene by hydroboration. The C5 and C18 chiral centers in these parts were created by the kinetic resolution of the racemic c-TMS allylic alcohols using the asymmetric epoxidation, while that of the C10-C14 part was constructed by the asymmetric hydrogen transfer reaction of the corresponding c-TMS acetylene ketone.

πŸ“œ SIMILAR VOLUMES

Total synthesis of Resolvin E1
Total synthesis of Resolvin E1
✍ Melissa Allard; Keith Barnes; Xuemei Chen; Yiu-Yin Cheung; Bryan Duffy; Charles πŸ“‚ Article πŸ“… 2011 πŸ› Elsevier Science 🌐 French βš– 449 KB

The enantioselective total synthesis of Resolvin E1 (RvE1), a naturally occurring small molecule mediator of inflammation resolution, is reported. Two routes are presented, both modular and convergent in nature, with an excellent control of all stereocenters. The C12-and C18-hydroxy groups are deriv

Total synthesis of resolvin E2
Total synthesis of resolvin E2
✍ Yusuke Kosaki; Narihito Ogawa; Yuichi Kobayashi πŸ“‚ Article πŸ“… 2010 πŸ› Elsevier Science 🌐 French βš– 589 KB

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 , an

A biogenetically patterned total synthes
A biogenetically patterned total synthesis of prostaglandin E1
✍ Chisato Sato; Shun'ichi Ikeda; Haruhisa Shirahama; Takeshi Matsumoto πŸ“‚ Article πŸ“… 1982 πŸ› Elsevier Science 🌐 French βš– 231 KB

Methyl ll-tert-butyldimethylsilyloxyeicosa-8~Z),l2~E),l4(E)trienoate was stereoselectively cyclized by treatment with Hg(OCOCF3j2 to give a properly functionalized PG skeleton, which was converted to PGEl in good over all yield.