Synthesis of (1S,2R,12S)-2-hydroxy-11-dihydroneocembrene

Autor:	Tadahiro Kato, Masahiro Hoshikawa, Shin-ichi Ebihara, Tohru Furukawa, Hirota Tanahashi
Rok vydání:	1999
Předmět:	Organic Chemistry Total synthesis Ether Grignard reagent Chloride Catalysis Coupling reaction Stereocenter Inorganic Chemistry chemistry.chemical_compound chemistry medicine Organic chemistry Physical and Theoretical Chemistry Geraniol Derivative (chemistry) medicine.drug
Zdroj:	Tetrahedron: Asymmetry. 10:3691-3700
ISSN:	0957-4166
Popis:	Aiming at the asymmetric total synthesis of trinervitane-type diterpenes, an efficient synthetic route to the title compound was explored starting from the THP ether of pivaloyloxy geraniol 11e. The coupling reaction with Grignard reagent 14 bearing the stereogenic carbon proceeded smoothly to give the THP ether of (11S)-10-dihydrogeranylgeraniol 10. Conversion to the corresponding acid chloride through the intermediate 9, followed by cyclization, afforded the dihydrocembrene derivative 8, from which the title compound 7 was prepared.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::739653fe8fc9f403a73823a4813a301c https://doi.org/10.1016/s0957-4166(99)00376-6 Zobrazit plný text záznamu Full Text from ScienceDirect