Asymmetric syntheses of the lactone core of tetrahydrolipstatin and tetrahydroesterastin and of the oriental hornet Vespa Orientalis pheromone

Abstract

A synthetic approach to the lactone core of the anti-obesity drugs tetrahydrolipstatin and tetrahydroesterastin has been developed starting from readily accessible methyl (5S)-5-{[tert-butyl(dimethyl)silyl]-oxy}-3-oxohexadecanoate. (6S)-6-Undecyltetrahydro-2H-pyran-2-one, the oriental hornet Vespa Orientalis pheromone, has also been synthesized. A formal synthesis of (3S,4R,6S)-dihydroxy-6-undecyltetrahydro-2Hpyran-2-one (metabolite of a fungus separated from mangrove seeds) has been proposed.

Recent advances in the synthesis of insect pheromones: an overview from 2013 to 2022

“…Fig. 9 shows the pheromones of Osmoderma eremita (Col., Cetoniidae): 194, 174,175 Nasonia vitripennis (Hym., Pteromalidae): 195, 176 Bactrocera tsuneonis (Dip., Tephritidae): 196, 177 Popillia japonica (Col., Scarabaeidae): (R)-197 and Anomala osakana (Col., Scarabaeidae): (S)-197, 178 Rhagoletis batava (Dipt., Tephritidae): 198, 179 Macrocentrus grandii (Hym., Braconidae): 199, 180 Vespa orientalis (Hym., Vespidae): 200, [181][182][183][184] Culex spp. (Dip., Culicidae): 201, [185][186][187][188][189] Phoracantha synonyma (Col., Cerambycidae): 202, 190 Silvestritermes minutus (Iso., Termitidae): 203, 191 Heliconius erato phyllis (Lep., Nymphalidae): 204 (anti-aphrodisiac).…”