334976-37-3Relevant articles and documents
A formal total synthesis of (-)-brevisamide, a marine monocyclic ether amide
Lee, Jungmee,Oh, Hong-Se,Kang, Han-Young
, 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 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.
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.
