ChemInform Abstract: Total Synthesis of (-)-Macrocarpal C. Stereoselective Coupling Reaction with a Novel Hexasubstituted Benzene Cr(CO)3 Complex as a Biomimetic Chiral Benzyl Cation Equivalent.
✍ Scribed by Tetsuaki Tanaka; Hidenori Mikamiyama; Kimiya Maeda; Chuzo Iwata; Yasuko In; Toshimasa Ishida
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 37 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0931-7597
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✦ Synopsis
Total Synthesis of (-)-Macrocarpal C. Stereoselective Coupling Reaction with a Novel Hexasubstituted Benzene Cr(CO) 3 Complex as a Biomimetic Chiral Benzyl Cation Equivalent. -The use of the novel chiral complex (II) allows for the stereocontrolled coupling with silyldienol ether (III) to obtain after decomplexation with CAN the coupling product (IV) with high diastereoselectivity. Neither the C-11 epimer nor a regioisomer are isolated. The enantiomeric complex of (II) reacts under analogous conditions to afford the C-aryl epimer of (IV) with the same high diastereoselectivity. The final deprotection of the three methoxy groups is successfully achieved by utilizing lithium p-thiocresolate as base. -(TANAKA, TETSUAKI; MIKAMIYAMA,