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- Title
Enantioselective Divergent Syntheses of Several Polyhalogenated Plocamium Monoterpenes and Evaluation of Their Selectivity for Solid Tumors.
- Authors
Vogel, Carl V.; Pietraszkiewicz, Halina; Sabry, Omar M.; Gerwick, William H.; Valeriote, Frederick A.; Vanderwal, Christopher D.
- 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.
- Subjects
MONOTERPENES; ACETONIDES; CELL lines; RED algae; NATURAL products
- Publication
Angewandte Chemie International Edition, 2014, Vol 53, Issue 45, p12205
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201407726