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ChemInform Abstract: Regioselective Transfer of the Prenyl Anion in the Total Synthesis of (.+-.)-Shikonin (IV).

โœ Scribed by De-Feng Xu; Li-Ming Zhao; Zhi-Qiang Mao; Shao-Shun Li


Publisher
John Wiley and Sons
Year
2008
Weight
18 KB
Volume
39
Category
Article
ISSN
0931-7597

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Regio- and Enantioselective Prenyl Anion
โœ Bor-Cherng Hong; Jang-Hsing Hong; Yann-Chien Tsai ๐Ÿ“‚ Article ๐Ÿ“… 1998 ๐Ÿ› John Wiley and Sons ๐ŸŒ English โš– 95 KB ๐Ÿ‘ 2 views

At elevated temperature (refluxing THF) prenyl anion adds regio- and enantioselectively to aldehyde 1 when a chiral, borneol-derived ligand is present. This reaction is the key stepin the first total synthesis of the monoterpene (-)-rosiridol (retrosynthesis is shown on the right). In addition, the