Details

Autor(en) / Beteiligte

• Hernández-Torres, Gloria
• Urbano, Antonio
• Carreño, M. Carmen
• Colobert, Françoise

Titel

Stereocontrolled Generation of the (2R) Chroman Core of Vitamin E: Total Synthesis of (2R,4′RS,8′RS)-α-Tocopherol

Ist Teil von

• Organic letters, 2009-11, Vol.11 (21), p.4930-4933

Ort / Verlag

United States: American Chemical Society

Erscheinungsjahr

2009

Quelle

MEDLINE

Beschreibungen/Notizen

• (2R,4′RS,8′RS)-α-Tocopherol (1) was prepared using, as the two key steps, a novel diastereoselective TiCl4-promoted (S)-sulfoxide-directed allylation of ketal 2 with allyl trimethyl silane 3 to efficiently generate the challenging (2R) stereocenter of the chroman moiety and a cross-metathesis reaction with olefin 4 to efficiently join the lipophilic alkyl chain present in the final target.