A common strategy for the synthesis of (+)-gabosine N, (+)-gabosine O, and some carbapyranoses using a Nozaki–Hiyama–Kishi reaction and RCM

Gram-scale carbasugar synthesis via intramolecular seleno-Michael/aldol reaction

“…Selective protection of primary hydroxyl group gave mixture of isomers 13 in 64% yield. Oxidation with Dess-Martin reagent in DCM to unsaturated ketone (14) and consecutive silyl ether deprotection gave 2,3,4-tri-O-benzylated (À)-gabosine E (15) in 84% yield in two steps (Scheme 5).…”

“…An application of monosaccharides to carbohydrate mimetic synthesis seems to be a natural choice. 12 General synthesis of carbasugars moieties is employing Grubbs cross metathesis reaction, [13][14][15][16] aldol-type cyclization, 17,18 Corey-Fuchs reaction 19 and others. 3 Total synthesis of gabosines has been recently reviewed by Mac and co-workers.…”

Role of the Nozaki–Hiyama–Takai–Kishi Reaction in the Synthesis of Natural Products

“…Many other products have been synthesized using NHTK to have access to gem -disubstituted alkenols, such as (+)-trachyspic acid, azaspiracid-1, polycavernoside A, , pteriatoxins, , kendomycin, (+)-gabosine N, lactodehydrothyrsiferol, moverastin analogs, (+)-pericosines A and B, , pleuromutilin, palhinine A, and (+)-pentandranoic acid A, among others (Figure ). In all these syntheses, NHTK cannot be considered the key step of the route, but it is still a useful tool to create C–C bonds under very mild conditions.…”

Enantioselective Synthesis of a New Non-Natural Gabosine

“…This wide range of biological properties turned the gabosine family into a group of coveted synthetic targets. During the last 30 years, several strategies have been developed to prepare gabosines [ 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 ] and related derivatives [ 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 ]. Among these and other synthetic efforts, only Banwell’s group and ours have applied biotransformations to introduce chirality into the process.…”