Lateral lithiation in terpenes: synthesis of (+)-ferruginol and (+)-sugiol

• Published in: Tetrahedron Vol. 66; no. 39; pp. 7773 - 7780
• Main Authors: Marcos, I.S., Beneitez, A., Moro, R.F., Basabe, P., Díez, D., Urones, J.G.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 25.09.2010; Elsevier
• Subjects: (−)-Sclareol; Abietanes; Alicyclic compounds, terpenoids, prostaglandins, steroids; Chemistry; Chemistry, Organic; Condensed benzenic and aromatic compounds; Diterpenes; Exact sciences and technology; Ferruginol; Lateral lithiation; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; Sugiol; Terpenoids; Sugiol; NEZNGQQBPXVPTD-FUHWJXTLSA-N; (−)-Sclareol; IPEHJNRNYPOFII-AZUAARDMSA-N; Ferruginol; KNOXYKYRMOOPNK-WIOPSUGQSA-N; XVULBTBTFGYVRC-HHUCQEJWSA-N; Diterpenes; Lateral lithiation; Abietanes; QXNWVJOHUAQHLM-AZUAARDMSA-N; CANCER CELLS; DIRECTED ORTHO-METALATION; FUNCTIONALIZATION; N,N'-DIARYLUREAS; BROMINATION; ABIETANE DITERPENES; CHEMISTRY; CONDENSATION; (-)-Sclareol; CYTOTOXICITY; DERIVATIVES; Terpenoid; Phenanthrene derivatives; Tricyclic compound; Terpene; Lithiation; Diterpene; Aromatic compound; Labdane derivatives; Chemical synthesis
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2010.07.066

This paper describes the use of (−)-sclareol in the synthesis of the tricyclic diterpenes of abietane skeleton, such as (+)-ferruginol and (+)-sugiol, using as key step the lateral lithiation of a dinorditerpene derivative. (+)-Ferruginol and (+)-sugiol have synthesised from (−)-sclareol, using lateral lithiation as key reaction. [Display omitted]