A Method for Easy Preparation of Optically Pure (S)-5-Hydroxy-2-penten-4-olide and (S)-5-Hydroxypentan-4-olide

Abstract

Oxidation of levoglucosenone (I) with m‐chloroperbenzoic acid in dichloromethane yields a mixture of the formyloxymethylbutenolide (II) and the carbonate (III).

Sustainable Synthesis and Polycondensation of Levoglucosenone‐Cyrene‐Based Bicyclic Diol Monomer: Access to Renewable Polyesters

“…To oxidize LGO‐Cyrene TM , our strategy relied on the well‐established Baeyer–Villiger oxidation. This well‐known reaction usually involves a peracid, such as meta ‐chloroperbenzoic acid ( m ‐CPBA) or peracetic acid, that reacts with a cyclic ketone to form an intermediate that rearranges into a lactone. Several groups have investigated the use of chemoenzymatic conditions to make this process greener and more sustainable.…”

Chemo-Enzymatic Synthesis of Chiral Epoxides Ethyl and Methyl (S)-3-(Oxiran-2-yl)propanoates from Renewable Levoglucosenone: An Access to Enantiopure (S)-Dairy Lactone

“…Recently, we reported on the eco-friendly synthesis of 2 by a chemo-enzymatic process from levoglucosenone (LGO) [21][22][23][24][25] a valuable chiral chemical platform obtained from flash pyrolysis of cellulosic residues, such as softwood sawdust (Furacell™ process) [26]. Providing 2 in very good yield and high purity through a lipase-based mediated oxidation, this sustainable synthetic pathway has been studied further by our group as an alternative to the one involving L-glutamic acid to achieve the synthesis of epoxides (S)-1a and (S)-1b (Scheme 2).…”

The Conversion of Levoglucosenone into Isolevoglucosenone

“…After g-lactonization and loss of C1 (levoglucosenone numbering) as a formate ion compound 6 would then be formed. Interestingly, the present work appears to represent the first time compound 6 has been reported to be formed directly from levoglucosenone rather than by a two-step process as described by Koseki et al [10] That having been said, the latter process is much more efficient.…”

“…In another attempt to effect the conversion 1 -3 and/or 4, the first of these compounds was treated with the same reagents as defined above but now at ambient temperatures and for a period of 336 h. Such conditions were investigated on the basis that the formation of ether 5 from levoglucosenone might be a reversible process and that there could, therefore, be a low steady-state concentration of the latter compound present in the reaction mixture that was available to engage in the desired nucleophilic epoxidation process. In the event, however, the only products isolated from the reaction mixture proved to be the previously reported hydroxymethylated butenolide 6 [10] (13 %) and the related methanol addition product 7 [11] (4 %). The former product is presumably derived from a Baeyer-Villiger type oxidation of substrate 1 to give an internal ortho-ester that is itself hydrolyzed under the alkaline conditions.…”

“…hexane/methanol) provided compound 6[10] (24 mg, 13 %) as a light yellow oil. n max (KBr)/cm À1 3400, 2932, 1745, 1602, 1331, 1170, 1112, 1080, 1053, 862, 820. d H (CDCl 3 , 500 MHz) 7.49 (m, 1H), 6.19 (m, 1H), 5.16 (m, 1H), 4.00 (dm, J 12.2, 1H), 3.78 (dd, J 12.2, 4.8, 1H), 2.64 (s, 1H).…”