Stereochemistry of terpene derivatives. Part 5: Synthesis of chiral lactones fused to a carane system—insect feeding deterrents

Autor:	Agata Białońska, Czesław Wawrzeńczyk, Katarzyna Ochalik, Bożena Frąckowiak, Stanisław Lochyński, Zbigniew Ciunik
Jazyk:	angličtina
Rok vydání:	2006
Předmět:	Inorganic Chemistry Terpene Chemistry Stereochemistry Organic Chemistry Diastereomer Moiety Organic chemistry Physical and Theoretical Chemistry Ring (chemistry) Catalysis Stereocenter
Zdroj:	Tetrahedron-Asymmetry. 17(1):124-129
ISSN:	0957-4166
DOI:	10.1016/j.tetasy.2005.11.025
Popis:	Chiral iodo- 9, bromo- 10 and hydroxylactones 12 condensed with the carane system were obtained. In each case, the synthetic pathway led to an enantiomerically pure diastereoisomer to generate two stereogenic centers. Iodo- 9 and bromolactone 10 possess a γ-lactone group while the hydroxylactone 12 possesses a δ-lactone moiety situated trans to the gem-dimethylcyclopropyl ring. The structures of the products were confirmed by X-ray crystallography. These lactones were tested for antifeedant activity against storage pest insects.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::1ac6d1aac62be34647baf3f74e2cb26c https://doi.org/10.1016/j.tetasy.2005.11.025 Zobrazit plný text záznamu Full Text from ScienceDirect