Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 45, Pages 12205-12209Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201407726
Keywords
antitumor agents; chlorination; olefination; stereocontrol; total synthesis
Categories
Funding
- NIH [R01 GM086483, F31 CA174176, R01 CA100851]
- UC Cancer Research Coordinating Committee
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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.
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