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Communication | Special issue | Vol 97, No. 2, 2018, pp.702-707
Published online, 9th March, 2018
DOI: 10.3987/COM-18-S(T)54
Synthetic Study of Thermolides: Stereoselective Construction of the C10-C21 Fragment

Hikaru Yoshimura, Jun Ishihara, and Susumi Hatakeyama*

*Medical Innovation Center, Nagasaki University, 1-14, Bunkyo-machi, Nagasaki 852-8521, Japan

Abstract

The C10-C21 fragment of nematocidal thermolides, macrocyclic PKS-NRPS hybrid metabolites isolated from a thermophilic fungus, was prepared in a highly stereoselective manner. The stereocontrol was accomplished by taking advantage of a cinchona alkaloid-catalyzed Morita-Baylis-Hillman reaction followed by diastereoselective hydrogenation and a cinchona alkaloid-catalyzed asymmetric β-lactone formation.