334976-37-3Relevant academic research and scientific papers
A formal total synthesis of (-)-brevisamide, a marine monocyclic ether amide
Lee, Jungmee,Oh, Hong-Se,Kang, Han-Young
supporting information, p. 1099 - 1102 (2015/02/19)
A formal total synthesis of (-)-brevisamide, a monocyclic ether amide with architecturally unique structural features, has been achieved. The tetrahydropyran core part of the target was synthesized by the aldol reaction followed by ring-closing metathesis using the Grubbs second generation catalyst. After the stereochemistry at the carbon center bearing the hydroxy group was adjusted, the carbon-carbon double bond was stereoselectively reduced by catalytic hydrogenation. Finally, introduction of the amino group was followed by acetylation, which provided the desired advanced intermediate.
Stereoselective total synthesis of cananginones (D-I) using Ireland-Claisen rearrangement as a key step
Kuilya, Tapan Kumar,Chatterjee, Shamba,Goswami, Rajib Kumar
, p. 2905 - 2918 (2014/04/17)
A strategy for stereoselective total synthesis of α-substituted γ-hydroxymethyl γ-butyrolactone containing bioactive natural products cananginones (D-I) has been developed using cheap and commercially available d-mannitol as a chiral pool. The Ireland-Cla
Stereoselective total synthesis of stagonolide-C
Venkatesham, Akkaladevi,Nagaiah, Kommu
, p. 1186 - 1197,12 (2020/09/09)
The highly stereoselective synthesis of a biologically active stagonolide-C has been described. The pivotal functionalities are derived from Barbier allylation, an epoxidation by m-CPBA, a chiral-auxiliary mediated acetate aldol addition, a 1,3-anti-reduction, a Sharpless kinetic resolution, a Yamaguchi macrolactonization, and ring-closing metathesis.
Stereoselective synthesis of the ABCD ring framework of azaspiracids
Yadav,Joyasawal, Sipak,Dutta,Kunwar
, p. 5335 - 5340 (2008/02/09)
A stereoselective synthesis of the ABCD ring framework of azaspiracid-1 and azaspiracid-3 has been achieved using a tandem bis-spiroketalization protocol in the presence of a mild proton source from 1,4-diketone precursor. A tetrahydrofuran intermediate w
A concise enantioselective synthesis of antimalarial febrifugine alkaloids.
Ooi,Urushibara,Esumi,Iwabuchi,Hatakeyama
, p. 953 - 955 (2007/10/03)
Reaction of (S)-2-(tert-butyldiphenylsilyloxy)-5-(mesyloxy)pentanal with hydroxylamine in allyl alcohol brought about simultaneous 1,3-dipolar cycloaddition of the resulting nitrone to allyl alcohol to give three diastereoisomeric adducts, from which (+)-febrifugine and (+)-isofebrifugine, potent antimalarial alkaloids, were synthesized.
