SYNTHESIS OF TREHAZOLIN FROM D-GLUCOSE

Trehazolin (2) is a specific inhibitor of trehalase, an enzyme that cl eaves the reserve carbohydrates of many insects. We describe a short a nd efficient synthesis of trehazolin (2) and trehazolamine (5) that mi mics its hypothetical biosynthesis. Starting molecule for the synthesi s of trehazolamine (5) is glucose from which three chiral centers are conserved during the reaction sequence. The remaining two chiral cente rs of trehazolamine (5) are formed stereoselectively in a reductive cy clization of ketooxime ether 16 and the reduction of oxime ether 18. T he overall yield of trehazolamine (5) is 22% over 8 steps from 15. The synthesis of trehazolin (2) from trehazolamine (5) follows a known pr ocedure and is achieved in 63% over 3 steps.