Total Synthesis of S-(+)-Argentilactone

2001 ◽  
Vol 56 (3) ◽  
pp. 325-328 ◽  
Author(s):  
Muhammad Saeed ◽  
Muhammad Abbas ◽  
Khalid Mohammad Khan ◽  
Wolfgang Voelter
Keyword(s):  
Total Synthesis ◽  
Wittig Reaction ◽  
Subsequent Oxidation

Abstract Asymmetrie Total Synthesis Asymmetrie total synthesis of S-(+)-argentilactone (2) was accomplished, using methyl-a-D-glucopyranoside (3) as carbohydrate template. Benzylidene acetal 5 was hydrolysed with tBuOOH/AlCl3 and further manipulated to produce the aldehyde 10. A Wittig reaction and subsequent oxidation of the anomeric position yielded the target argentilactone.

Domino Primary Alcohol Oxidation-Wittig Reaction: Total Synthesis of ABT-418 and (E)-4-Oxonon-2-enoic Acid

Synthesis ◽  
2004 ◽  
Vol 2004 (11) ◽  
pp. 1859-1863 ◽  
Author(s):  
Santosh Tilve ◽  
Jyoti Shet ◽  
Vidya Desai
Keyword(s):  
Total Synthesis ◽  
Wittig Reaction ◽  
Primary Alcohol ◽  
Alcohol Oxidation ◽  
Enoic Acid

scholarly journals A Concise and Efficient Total Synthesis of α-Mangostin and β-Mangostin from Garcinia Mangostana

2013 ◽  
Vol 8 (8) ◽  
pp. 1934578X1300800
Author(s):  
Dandan Xu ◽  
Ying Nie ◽  
Xizhou Liang ◽  
Ling Ji ◽  
Songyuan Hu ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Wittig Reaction ◽  
Claisen Rearrangement ◽  
Practical Approach ◽  
Efficient Synthesis ◽  
Garcinia Mangostana ◽  
Diverse Groups

The concise, efficient synthesis of α-mangostin is described in eight simple steps with 8.3% overall yield. Highlights include a practical approach to construct the isopentene groups and other diverse groups at C–2 and C–8 of the xanthene skeleton through Claisen rearrangement and Wittig reaction. Meanwhile the first total synthesis of β-mangostin is presented with a similar approach.

scholarly journals Total synthesis of the endogenous inflammation resolving lipid resolvin D2 using a common lynchpin

2013 ◽  
Vol 9 ◽  
pp. 2762-2766 ◽  
Author(s):  
John Li ◽  
May May Leong ◽  
Alastair Stewart ◽  
Mark A Rizzacasa
Keyword(s):  
Total Synthesis ◽  
Wittig Reaction ◽  
Phosphonium Salt ◽  
Ester Hydrolysis ◽  
Sonogashira Coupling ◽  
Partial Reduction ◽  
Vinyl Iodide ◽  
Key Steps

The total synthesis of the endogenous inflammation resolving eicosanoid resolvin D2 (1) is described. The key steps involved a Wittig reaction between aldehyde 5 and the ylide derived from phosphonium salt 6 to give enyne 17 and condensation of the same ylide with aldehyde 7 to afford enyne 11. Desilylation of 11 followed by hydrozirconation and iodination gave the vinyl iodide 4 and Sonogashira coupling between this compound and enyne 3 provided alkyne 18. Acetonide deprotection, partial reduction and ester hydrolysis then gave resolvin D2 (1).

Formal total synthesis of salvianolic acid N

2018 ◽  
Vol 16 (5) ◽  
pp. 832-837 ◽  
Author(s):  
Kong Wu ◽  
Zhong Pao Xie ◽  
Dong-Mei Cui ◽  
Chen Zhang
Keyword(s):  
Total Synthesis ◽  
Intramolecular Cyclization ◽  
Wittig Reaction ◽  
Membered Ring ◽  
Salvianolic Acid

Salvianolic acid N was synthesized starting from 3,4-dimethoxybenzaldehyde in 11 steps and with an overall yield of 11%. The key reaction steps were the Wittig reaction for Z-stereoselectivity, the copper catalyzed intramolecular cyclization for seven membered ring skeleton, and the deprotected allylic group with Pd catalysis.

scholarly journals Stereoselective Synthesis of Maresin-Like Lipid Mediators

Synlett ◽  
2019 ◽  
Vol 30 (03) ◽  
pp. 343-347 ◽  
Author(s):  
Song Hong ◽  
Yan Lu ◽  
Masao Morita ◽  
Shun Saito ◽  
Yuichi Kobayashi ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Wittig Reaction ◽  
Kinetic Resolution ◽  
Stereoselective Synthesis ◽  
Lipid Mediators ◽  
Allylic Alcohol ◽  
Hexaenoic Acid ◽  
Asymmetric Epoxidation ◽  
Epoxy Alcohol ◽  
Activated Macrophage

14S,22-Dihydroxy-docosa-4Z,7Z,10Z,12E,16Z,19Z-hexaenoic acid (maresin-L1) and 14R,22-dihydroxy-docosa-4Z,7Z,10Z, 12E,16Z,19Z-hexaenoic acid (maresin-L2) were chemically synthesized. They were identical to activated macrophage-produced counterparts and their total synthesis was highly stereoselective, as revealed by chiral LC-UV-MS/MS analysis. The synthesis involved the following steps: (1) kinetic resolution of a racemic allylic alcohol by the asymmetric epoxidation; (2) transformation of the epoxy alcohol to γ-hydroxyenal derivative; and (3) the Wittig reaction to furnish the Z-olefin.

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