1243054-22-9Relevant academic research and scientific papers
Stereoselective Synthesis of Highly Substituted Conjugated Dienes via Pd-Catalyzed Carbonylation of 1,3-Diynes
Liu, Jiawang,Yang, Ji,Baumann, Wolfgang,Jackstell, Ralf,Beller, Matthias
, p. 10683 - 10687 (2019/07/04)
The stereoselective synthesis of conjugated dienes was realized for the first time via Pd-catalyzed alkoxycarbonylation of easily available 1,3-diynes. Key to success is the utilization of the specific ligand 1,1′-ferrocenediyl-bis(tert-butyl(pyridin-2-yl)phosphine) (L1), which allows this novel transformation to proceed at room temperature. A range of 1,2,3,4-tetrasubstituted conjugated dienes are obtained in this straightforward access in high yields and selectivities. The synthetic utility of the protocol is showcased in the concise synthesis of several important intermediates for construction of natural products rac-cagayanin, rac-galbulin, rac-agastinol, and cannabisin G.
Total synthesis of (±)-agastinol
Ding, Junwei,Zhou, Haitang,Jiao, Bin,Xia, Yamu
, p. 352 - 354 (2011/10/08)
A synthesis of the tetrahydrofuran lignan (±)-agastinol, starting from the cheap Vanillin, has been developed based on Stobbe reaction with diethyl succinate to give the skeleton of lignan, which was then reduced to afford meso- and threo-(±)-secoisolanciresinol. threo-(±)- Secoisolanciresinol was treated with DDQ in acetic acid to give the 2-aryl tetrahydrofuran lignan, and which was then condensed with ferulic acid to give (±)-agastinol for the first time.
Synthesis of threo-(±)-9,9-dibenzoylsecoisolariciresinol and its isomer
Xia, Yamu,Wen, Yanling
experimental part, p. 606 - 609 (2011/02/28)
The total synthesis of threo-(±)-9,9-dibenzoylsecoisolariciresinol and its isomer based on two Stobbe reactions as C-C bond-forming steps used a protected vanillin and diethyl; succinate to give the skeleton of lignan, followed by reduction to afford threo-and meso-(±)-secoisolariciresinol Both were treated with benzoyl chloride to obtain the natural product threo-(±)-9,9-dibenzoylsecoisolariciresinol and Its isomer meso-(±)-9,9-dibenzoylsecoisolariciresinol for the first time.
Total synthesis of (±)-divanillyltetrahydrofuran ferulate
Xia, Ya-Mu,You, Jia,Wang
scheme or table, p. 433 - 436 (2010/12/25)
A convenient method for the synthesis of sesquilignan threo- and erythro-(±)-divanillyltetrahydrofuran ferulate is described. The synthesis was based on a unified synthetic strategy involving two Stobbe condensations to give the skeleton of lignan, and then reduction reaction to form meso- and threo-(±)-secoisolanciresinol. meso- and threo-(±)-secoisolanciresinol were separated by flash column chromatography, followed by intramolecular reaction with TsCl to afford the key intermediate meso- or threo-(±)-shonanin, then condensation with ferulaic acid to obtain sesquilignan threo- or its analogue erythro-(±)- divanillyltetrahydrofuran ferulate. Indian Academy of Sciences.
