Structure of a novel macrodiolide antibiotic IKD-8344

Synthesis of Enantiopure Termini-Differentiated Heptane Stereotriads.1 Application to Side Chain-Functionalized Tetrahydrofurans of IKD-8344

“…For example, IKD-8344 9 (Figure 2) is a C 2 symmetric 28-membered ring diolide which appears to have potential as an anticancer agent. 5 The secoacid segments of 9 can be envisioned to arise from one molecule of the enantiomer of enantiopure anti-7b and two molecules of syn-7b.…”

“…In addition to using the cyclic vinyl sulfones as direct precursors of termini-differentiated acyclic heptyl fragments analogous to the hexyl compounds, these materials can also serve as precursors of side chain-functionalized monocyclic intermediates . For example, IKD-8344 9 (Figure ) is a C 2 symmetric 28-membered ring diolide which appears to have potential as an anticancer agent . The secoacid segments of 9 can be envisioned to arise from one molecule of the enantiomer of enantiopure anti-7b and two molecules of syn-7b .…”

Applications of Wittig Reaction in the Total Synthesis of Natural Macrolides

“…8344 having active anthelmintic property against Trichinella spiralis and potent cytotoxicity against L5178Y mouse leukemia cells. [253] IKD-8344 236 was isolated from Streptomyces sp. A6792 and also exhibited selective antifungal properties against the mycelial form of Candida albicans.…”