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Stereocontrolled Total Synthesis of Nonenolide.
Journal of Natural Products 2018 June 23
Nonenolide (1) was first isolated from the entomopathogenic fungus Cordyceps militaries BCC2816 and exhibited good antimalarial activity against Plasmodium falciparum K1. Structurally, it features a decanolide with a trans-double bond attached to two chiral hydroxy groups, making the total synthesis of the exclusive isomer of 1 more difficult. Herein, we report the successful synthesis of 1 by employing a MacMillan α-hydroxylation to generate three chiral centers in both the key fragments, starting from 1,6-hexanediol and 1,4-butanediol, followed by Steglich esterification of compounds 2 and 3. The exclusive E-isomer was obtained via a ring-closing metathesis of the mono-PMB-protected diene 19. Deprotection provided the required natural product 1.
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