A novel entry to naturally occurring 5-alkenyl α,β-unsaturated δ-lactones from d-glucose: syntheses of (+)-acetylphomalactone and (+)-asperlin

A Survey of Recent Synthetic Applications of 2,3-Dideoxy-Hex-2-enopyranosides

“…For example, ethyl 2,3-dideoxy-α- d -erythro-hex-2-enopyranoside ( 94 , R=Et) undergoes chemoselective allylic oxidation upon treatment with manganese dioxide or pyridinium dichromate to give hex-2-enopyranoside-4-ulose 95 , whereas selective oxidation of the primary hydroxyl group can be effected by a modification of the Corey-Kim procedure [103], as recommended by Fraser-Reid and co-workers, leading to aldehyde 96 [104,105,106]. The latter compound (R = Et) was used in a stereoselective synthetic approach to (+)-asperlin [107].…”

Enantioselective Syntheses of Isoaltholactone, 3-epi-Altholactone, and 5-Hydroxygoniothalamin

“…These natural products have biological activity including antitumor 1a and antifungal properties,1f as well as antibiotic potential 1f. Due to the wide distribution of 5,6-dihydro-2 H -pyran-2-ones in plants and fungi, many synthetic methodologies have been employed to synthesize this core structure. , …”

Synthetic Approaches to α,β‐Unsaturated δ‐Lactones and Lactols

“…As a result of some similarities between sugars and some naturally occurring polyhydroxylated α,β-unsaturated δ-lactones, the use of sugar derivatives as chiral building blocks in the multi-step total syntheses of argentilactone, [59] anamarine, [60] asperlin, [61] and acetylphomalactone [61] has been widely studied. This topic is beyond the scope of this review and so is not covered here.…”