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

TitleEnantioselective divergent syntheses of several polyhalogenated plocamium monoterpenes and evaluation of their selectivity for solid tumors
Publication TypeJournal Article
Year of Publication2014
AuthorsVogel C.V, Pietraszkiewicz H., Sabry O.M, Gerwick WH, Valeriote F.A, Vanderwal C.D
JournalAngewandte Chemie-International Edition
Volume53
Pagination12205-12209
Date Published2014/11
Type of ArticleArticle
ISBN Number1433-7851
Accession NumberWOS:000344052000037
Keywordsallylic alcohols; antitumor agents; aplysia-californica; chlorination; chlorosulfolipids; cornutum; dichlorination; halogenated monoterpenes; malhamensilipin; mytilipin; olefination; stereocontrol; stereoselectivity; synthesis; total
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.

DOI10.1002/anie.201407726
Short TitleAngew. Chem.-Int. Edit.
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