Abstract
Acrylic esters of homoallylic alcohols prepared in 92-96% ee via the asymmetric allylboration of appropriate aldehydes with B-allyldiisopinocampheylborane, upon ring-closing metathesis in the presence of 10mol% of Grabbs' catalyst provided the corresponding 6-substituted dihydropyran-2-ones. These were diastereoselectively epoxidized and regioselectively reduced to furnish optically pure analogs of statin drugs. This procedure allows for the development of a combinatorial library of analogs of these drugs.
Original language | English (US) |
---|---|
Pages (from-to) | 239-243 |
Number of pages | 5 |
Journal | Journal of Organometallic Chemistry |
Volume | 624 |
Issue number | 1-2 |
DOIs | |
State | Published - Apr 1 2001 |
Bibliographical note
Funding Information:Financial assistance from the Purdue Borane Research Fund is gratefully acknowledged.
Keywords
- Allylboration
- Asymmetric synthesis
- Epoxidation
- Metathesis
- Reduction