Radical reactions on pinene-oxide derivatives induced by Ti(III)

• Published in: Tetrahedron Vol. 67; no. 49; pp. 9529 - 9534
• Main Authors: Fernandez-Mateos, A., Herrero Teijon, P., Rubio Gonzalez, R.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 09.12.2011; Elsevier
• Subjects: Alicyclic compounds, terpenoids, prostaglandins, steroids; Chemistry; Chemistry, Organic; Chlorides; Derivatives; Epoxides; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Materials selection; Organic chemistry; Oxides; Physical Sciences; Pinene-derived terpenoids; Preparations and properties; Radical reactions; Radicals; Science & Technology; Synthesis (chemistry); Terpenoids; Tetrahedrons; Titanocene; α-Pinene oxide; LCYXQUJDODZYIJ-VGMNWLOBSA-N; LOVCVWMKXWSJMH-MTFIHPLSSA-N; DCSCXTJOXBUFGB-JGVFFNPUSA-N; REPVLJRCJUVQFA-HXFLIBJXSA-N; FFOYLHBMVUGHSX-SNVBAGLBSA-N; α-Pinene oxide; RXIPIXBCYCZRKR-NEPJUHHUSA-N; RXBQNMWIQKOSCS-IUCAKERBSA-N; UWAYVQLYWONCAM-HNCHTBHHSA-N; NDTYTMIUWGWIMO-SNVBAGLBSA-N; Titanocene; IZVTYOJWVVOBBO-IVZWLZJFSA-N; Radical reactions; PFGFINDRFRTQEP-IVZWLZJFSA-N; FZXLDENMTYEVAD-ZJUUUORDSA-N; Pinene-derived terpenoids; IFFMOZVTULZCLO-SCZZXKLOSA-N; BAVONGHXFVOKBV-ZJUUUORDSA-N; Epoxides; SFEGOGKROCHYRO-SCZZXKLOSA-N; OXIDATION; TERPENES; CONVERSION; NATURAL-PRODUCTS; ISOMERIZATION; alpha-Pinene oxide; REARRANGEMENT; ALPHA-PINENE; ELECTRON-TRANSFER; SELENIUM DIOXIDE; Terpenoid; Selectivity; Oxygen heterocycle; Organic chlorine compounds; Metallocene; Free radical reaction; Titanium III; Terpene; Titanium Organic compounds; Epoxide; Monoterpene; Pinene; Chemical synthesis
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2011.10.004

A practical, brief and selective synthesis of several pinene oxide derived terpenoids can be achieved from readily available starting materials. The key step is a radical reaction promoted by titanocene chloride. [Display omitted]