115463-10-0Relevant articles and documents
Assembly of the southern macrocyclic half of (+)-spirastrellolide a through cyclic acetal tethered ring-closing metathesis and 1,3-anti-mukaiyama-aldol
Tang, Yu,Yang, Jin-Haek,Liu, Jia,Wang, Chao-Chao,Lv, Ming-Can,Wu, Yi-Biao,Yu, Xue-Liang,Ko, Changhong,Hsung, Richard P.
, p. 565 - 598 (2013/08/23)
We describe herein details of our efforts in syntheses of A-ring and BC-ring of (+)-spirastrellolide A. While the former would constitute a facile 12-step synthetic endeavor starting from 1,5-pentanediol, the latter would showcase a cyclic acetal-tethered
Stereoselective total synthesis of putaminoxin
Yadav, Jhillu Singh,Raju, Ande,Ravindar, Kontham,Reddy, Basi V. Subba,Khazim Al Ghamdi, Ahmad Al
experimental part, p. 585 - 590 (2012/04/04)
The stereoselective total synthesis of a phytotoxic macrolide putaminoxin, isolated from the culture of Phoma putaminum fungus, has been accomplished by utilization of Sharpless asymmetric epoxidation, Birch reduction, Jacobsens kinetic resolution of race
A practical total synthesis of (+)-spirolaxine methyl ether
Yadav,Sreenivas,Srinivas Reddy,Subba Reddy
supporting information; experimental part, p. 8307 - 8310 (2011/02/27)
An efficient and practical total synthesis of (+)-spirolaxine methyl ether is described. The phthalide-aldehyde 3 has been prepared via the Diels-Alder reaction between 1,4-unconjugated diene 5 and a long-chain acetylenic dienophile 6. The carbon framework of spiroketal sulfone 4 has been constructed from monobenzyl protected 1,5-pentanediol and the stereochemistry in both the phthalide portion and the spiroketal portion has been established by the Sharpless asymmetric epoxidation.
Concise synthesis of stagonolide-F by ring closing metathesis approach and its biological evaluation
Perepogu, Arun Kumar,Raman,Murty,Rao, Vaidya Jayathirtha
scheme or table, p. 46 - 51 (2009/08/07)
The first total synthesis of 9-membered macrolide, stagonolide-F (3), starting from commercially available 1,5-pentane diol is reported. A combination of Jacobsen's hydrolytic kinetic resolution (HKR) and Sharpless epoxidation is used for the creation of two stereogenic centers, while ring-closing metathesis (RCM) strategy was used for the construction of the lactone ring. The molecule synthesized exhibited potent antifungal, antibacterial and cytotoxic activities against all the tested strains.
Diazo reagents in copper(I)-catalyzed olefination of aldehydes
Lebel, Helene,Davi, Michael
supporting information; experimental part, p. 2352 - 2358 (2009/10/02)
The olefination of aldehydes to synthesize unsaturated ketones, esters, amides and phosphonates using diazo reagents and triphenylphosphine in the presence of copper(I) iodide as catalyst, is described. Good to excellent E:Z selectivities as well as yields were obtained for a large variety of aliphatic, aromatic and heteroaromatic aldehydes. The reaction showed also an excellent functional group compatibility and aldehydes were selectively reacted in the presence of ketone, nitro, amine, ether, acetal, thioether and halide groups. The use of a cost-effective copper salt as a catalyst is advantageous compared to previously reported expensive transition metal complexes. The method was used in the total synthesis of the scutifoliamide A, a biologically active compound that exhibits antifungal activity.
Novel and stereoselective synthesis of (+)-lentiginosine
Raghavan, Sadagopan,Sreekanth
, p. 565 - 570 (2007/10/03)
The stereoselective synthesis of (+)-lentiginosine, a potent amyloglucosidase inhibitor, is disclosed exploiting the potential of the sulfinyl moiety as an internal nucleophile to regio- and stereoselectively functionalize an olefin.
Synthesis of fused bicyclic glutarimides
Chang, Meng-Yang,Chen, Chung-Yi,Chen, Shui-Tein,Chang, Nein-Chen
, p. 7547 - 7553 (2007/10/03)
We describe an efficient route towards the synthesis of fused bicyclic glutarimides using facile [3+3] reaction of α-sulfonylacetamides with different α,β-unsaturated esters as the key step. Intramolecular cyclization of 4-substituted 3-sulfonylglutarimide to form 5,6-, 6,6- or 6,7-fused bicyclic glutarimides was accomplished via alkylation, oxidative cyclization or ring-closing metathesis in modest yield.
Synthetic study of 4-substituted piperidine ring in elarofiban, RWJ-50042, tirofiban and paroxetine
Chang, Meng-Yang,Lin, John Yi-Chung,Chen, Shui-Tein,Chang, Nein-Chen
, p. 1079 - 1088 (2007/10/03)
A new strategy for synthesizing a 4-substituted piperidine ring uses the formal [3+3] cycloaddition reaction as the key protocol. This method provides a convenient formal synthesis of elarofiban, RWJ-50042, tirofiban and paroxetine.
