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Regio- and Enantioselective Prenyl Anion Transfer: Application to the Total Synthesis of (−)-Rosiridol

✍ Scribed by Bor-Cherng Hong; Jang-Hsing Hong; Yann-Chien Tsai

Publisher
John Wiley and Sons
Year
1998
Tongue
English
Weight
95 KB
Volume
37
Category
Article
ISSN
0044-8249

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✦ Synopsis

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 absolute configuration of this natural product has been assigned conclusively. M=Zn, R=tBuMe Si.

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