Syntheses of hydroxy ketones from lactones

Synthesis of 15N‐labelled nornicotine and 15N‐labelled nicotine

“…13 Oxidation of the alcohol 5 in mild conditions using the Swern method 14 led to the ketoaldehyde 4 which was immediately used in the next step without purification (Scheme 3).…”

Research Progress in the Pharmacological Effects and Synthesis of Nicotine

“…Huang and co‐workers reported an efficient approach to the synthesis of rac‐nicotine (Scheme 11). [77] 3‐bromopyridine ( 46 ) was treated with BuLi by halogen‐lithium exchange, and then the γ‐butyrolactone ( 47 ) was added to afford the hydroxyketone 48 [78] . Diol 49 was given by the reduction of 48 with NaBH 4 , and then reacted with methanesulfonyl chloride in the presence of Et 3 N to afford dimesylate 50 .…”

“…Loh and co‐workers reported a four‐step stereoselective synthesis of ( S )‐ 3 (Scheme 16). [88] 48 described above was afforded for aldehyde 37 by Swern oxidation [77,78] . 69 was afforded by the diastereoselective reductive aminocyclization with 2,3,4,6‐tetra‐ O ‐pivaloyl‐β‐D‐galactosylamine ( 68 ), [89] which showed the effect of chiral additives.…”

“…[88] 48 described above was afforded for aldehyde 37 by Swern oxidation. [77,78] 69 was afforded by the diastereoselective reductive aminocyclization with 2,3,4,6-tetra-Opivaloyl-β-D-galactosylamine (68), [89] which showed the effect of chiral additives. By the acidic hydrolysis of 69, pure (S)-3 was afforded in 95 % yield.…”

Synthesis of Differently Protected 1‐C‐Methyl‐Ribofuranoses Intermediates for the Preparation of Biologically Active 1′‐C‐Methyl‐Ribonucleosides

“…[6,7,11] Opening of the ribonolactone to the corresponding methyl ketone and related formation of a tertiary alcohol reported for other lactones [22] were not observed in the case of lactone 5. [23] We have verified that 8 presents only the a-OH and have not observed the formation of other competing side products.…”