164524-20-3Relevant academic research and scientific papers
Stereocontrolled total synthesis of Neuroprotectin D1/Protectin D1 and its aspirin-triggered stereoisomer
Petasis, Nicos A.,Yang, Rong,Winkler, Jeremy W.,Zhu, Min,Uddin, Jasim,Bazan, Nicolas G.,Serhan, Charles N.
scheme or table, p. 1695 - 1698 (2012/05/05)
Neuroprotectin D1/Protectin D1, a potent anti-inflammatory, proresolving, and neuroprotective lipid mediator derived biosynthetically from docosahexaenoic acid, was prepared in an enantiomerically pure form via total organic synthesis. The synthetic strategy is highly stereocontrolled and convergent, featuring epoxide opening of glycidol starting materials for the introduction of the 10(R) and 17(S) hydroxyl groups. The desired alkene Z geometry was secured via the cis-reduction of alkyne precursors, while the conjugated E,E,Z triene was introduced at the end, in order to minimize Z/E isomerization. The same strategy, was also employed for the total synthesis of aspirin-triggered neuroprotectin D1/protectin D1 having the 17(R)-stereochemistry. Synthetic compounds obtained with the reported method were matched with endogenously derived materials, and helped establish their complete stereochemistry.
Total Synthesis of Halicholactone and Neohalicholactone
Critcher, Douglas J.,Connolly, Stephen,Wills, Martin
, p. 6638 - 6657 (2007/10/03)
The total synthesis of the marine natural products neohalicholactone (1) and halicholactone (2), in enantiomerically pure form, are reported. Key steps in the synthesis of each compound include a cis-selective Wittig reaction, stereoselective cyclopropanation, nine-membered lactone formation using the Yamaguchi method and late-stage stereoselective Cr(II)/Ni(II) mediated coupling of vinyl iodides 39 and 50 with aldehyde 14. In the case of the neohalicholactone synthesis the two major components which were coupled in this convergent synthesis were each derived from the enantiomers of commercially available malic acid. The synthesis served to confirm the original assignment of absolute configuration which was made by Yamada and Clardy. We also demonstrated, through the preparation of diastereoisomers, that another reported compound closely related to neohalicholactone is likely to be the C-15 epimer 67.
The total asymmetric synthesis of halicholactone and neohalicholactone
Critcher, Douglas J.,Connolly, Stephen,Wills, Martin
, p. 3763 - 3766 (2007/10/02)
Completion of the first total synthesis of the marine natural products Halicholactone and Neohalicholactone is reported. The key step is a moderately stereoselective coupling between a vinylic anion and an aldehyde. An unexpectedly slow desilylation due t
