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Enantioselective Divergent Syntheses of Several Polyhalogenated Plocamium Monoterpenes and Evaluation of Their Selectivity for Solid Tumors |
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| Authors: | Carl V. Vogel Halina Pietraszkiewicz Omar M. Sabry Prof. William H. Gerwick Dr. Frederick A. Valeriote Prof. Christopher D. Vanderwal |
| Affiliation: | 1. 1102 Natural Sciences II, Department of Chemistry, University of California, Irvine, Irvine, CA 92697 (USA);2. Division of Hematology and Oncology, Department of Internal Medicine, Henry Ford Hospital, Detroit, MI 48202 (USA);3. College of Pharmacy, Oregon State University, Corvallis, OR 97331 (USA);4. Current address: College of Pharmacy, Cairo University, Cairo, 11562 (Egypt);5. Center for Marine Biotechnology and Biomedicine, Scripps, Institution of Oceanography, University of California, San Diego, La Jolla, CA 92093 (USA) |
| Abstract: | The family of polyhalogenated monoterpenes from Plocamium counts over a hundred known members. Using glyceraldehyde acetonide as a chiral‐pool precursor, an enantioselective and divergent strategy was developed that provides a blueprint for the synthesis of many of the small yet complex acyclic members of this family. The broad applicability of this approach is demonstrated with the short, eight‐step synthesis of four natural products and three analogues. These syntheses are the first of any members of the acyclic polyhalogenated Plocamium monoterpenes and permitted the evaluation of their selectivity against a range of tumor cell lines. |
| Keywords: | antitumor agents chlorination olefination stereocontrol total synthesis |