Enantioselective divergent syntheses of several polyhalogenated Plocamium monoterpenes and evaluation of their selectivity for solid tumors.

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.

• Authors: Carl V Vogel, Halina Pietraszkiewicz, Omar M Sabry, William H Gerwick, Frederick A Valeriote, Christopher D Vanderwal
• Journal: Angewandte Chemie (International ed. in English) (Angew Chem Int Ed Engl) Vol. 53 Issue 45 Pg. 12205-9 (Nov 03 2014) ISSN: 1521-3773 [Electronic] Germany
• PMID: 25220828 (Publication Type: Journal Article, Research Support, N.I.H., Extramural, Research Support, Non-U.S. Gov't)
• Copyright: © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Chemical References

• Monoterpenes

Topics

• HCT116 Cells
• Humans
• Monoterpenes (chemical synthesis, therapeutic use)
• Neoplasms (drug therapy)
• Plocamium (chemistry)
• Stereoisomerism