Diastereoselective allylation of N-glyoxyloyl-(2R)-bornane-10,2-sultam and (1R)-8-phenylmenthyl glyoxylate: synthesis of (2S,4S)-2-hydroxy-4-hydroxymethyl-4-butanolide

Facile Synthesis of Enantiopure 4‐Substituted 2‐Hydroxy‐4‐ butyrolactones using a Robust Fusarium Lactonase

“…Ito et al assigned3 the AS of natural product (+)‐harzialactone A (4‐benzyl 2‐hydroxy‐4‐butyrolactone) using the Mosher ester method but the results were challenged by Mereyala et al 3. Kiegiel et al established the configuration of chiral 4‐methyl 2‐hydroxy‐4‐butyrolactone unambiguously by transforming this compound into its derivative which could crystallize to afford the single crystals suitable for X‐ray analysis 20. However, this method is limited to crystalline compounds (or its derivatives) only.…”

Synthesis of 3′‐Deoxyribolactones using a Hydrolysis‐Induced Lactonization Cascade Reaction of Epoxy Cyanohydrins

“…Subsequent hydrolysis of the TBS‐protected cyanohydrin and intramolecular lactonization in the usual manner result in the optically pure chloromethyl lactones (2 R ,4 R )‐ and (2 R ,4 S )‐ 4c in excellent yields starting from (2 R ,4 R )‐ and (2 R ,4 S )‐ 13a , respectively. Such optically pure halomethyl γ‐lactones are useful synthetic intermediates towards a range of biologically active chiral 4‐butanolides 6,7…”

“…Suitably functionalized lactones are generally considered convenient precursors to access these types of carbohydrates 5. For example chiral sultams have been employed to efficiently give diastereomeric mixtures of 3′‐deoxyribolactones 7,8. Another approach describes the asymmetric synthesis of 3′‐deoxyribolactones from γ,δ‐unsaturated α‐hydroxy esters as common precursor 9.…”

Stereoselective α-Hydroxylation of Amides Using Oppolzer’s Sultam as Chiral Auxiliary

“…(R)-1-((3aS,6R,7aR)-8,8-Dimethyl-2,2-dioxidotetrahydro-3H-3a,6methanobenzo [c]isothiazol-1(4H)-yl)-2-hydroxypent-4-en-1-one (7q). 21 The title compound was prepared by the general synthesis on a 0.34 mmol scale and obtained in 75% yield (79.1 mg) as a white solid after column chromatography (PE/EA = 8:1). dr > 20:1; [α] D 25 −80.1 (CHCl 3 , c = 0.76); M.p.…”