The family of acyclic polyhalogenated monoterpenes from the red algae <i>Plocamium</i> includes dozens of known members with differing stereochemistry of vicinal dichlorides, and a wide variety of halogenaiton patterns. We have developed a strategy that takes advantage of glyceraldehyde acetonide as a chiral-pool precursor, allowing the enantioselecitve, divergent syntheses of these natural products. The divergent nature of the synthesis allows us not only access to multiple diasteriomers and halogenation patterns, but an opportunity to synthesize unnatural analogues for biological evaluation. To date, five natural products and four unnatural analogues have been synthesized. A number of these compounds have been screened against a variety of solid tumor cell lines, showing selectivity for several solid tumor cell lines over leukemia cell lines.

Syntheses of acyclic polyhalogenated <i>Plocamium</i> monoterpenes and evaluation of activity for solid tumors

249th National Meeting (2015)

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Syntheses of acyclic polyhalogenated Plocamium monoterpenes and evaluation of activity for solid tumors