Double-Edged Synthesis

Double-Edged Synthesis

Author: David Bradley

Matthew Shair and colleagues, Harvard University, USA, have developed a novel strategy that allowed them to construct, and then characterize for the first time, the hibarimicins, including hibarimicinone (pictured). These pseudodimeric type-II polyketides were originally isolated from a culture broth of the rare actinomycete Microbispora rosea and have been shown to block the proliferation of a wide range of cancer cell types in the laboratory.

The team exploited a newly devised benzyl fluoride Michael–Claisen reaction sequence to build the complete carbon skeleton of two of these molecules, HMP-Y1 and atrop-HMP-Y1. Symmetrical, two-directional, double annulations allowed them to pull together the two halves of the molecule, each of which bears four fused carbon rings. The total synthesis required only a further three to five steps after this double annulation to make the final product and a related compound.

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