Abstract
Two alternative synthetic strategies for the synthesis of vicinal amino alcohols from naturally occurring amino acids have been investigated, viz. one going through diastereoselective addition of organometallic species to an amino aldehyde and one going through α'-chiral α,β-enones and their diastereoselective reduction. Based on these investigations we were able to develop a synthetic strategy towards all diastereomers of deoxynojirimycin starting from naturally occurring serine through a divergent route with a late stage intermediate that can be prepared in large quantities and in enantiomerically pure form.
| Original language | English |
|---|---|
| Pages (from-to) | 609-623 |
| Number of pages | 15 |
| Journal | Heterocycles |
| Volume | 103 |
| Issue number | 2 |
| Early online date | 22 Jan 2021 |
| DOIs | |
| Publication status | Published - 2021 |
| MoE publication type | A2 Review article, Literature review, Systematic review |
Funding
The results presented in this review are the product of a large number of students in my group over the years. I wish to thank the able students B.Sc. Jane Paul, Ph.D. P?ivi Koskinen, Ph.D. Oili Kallatsa, Ph.D. Mikko Passiniemi, Ph.D. Oskari Karjalainen, and Ph.D. Saara Tiuri for their skilled execution of this research. Skillful technical support for analyses have been provided by P?ivi Joensuu (University of Oulu) and Tiia Sepp? (Aalto University). For NMR experiments, Dr. Jari Koivisto has been instrumental in providing not only help, but also new pulse sequences. Funding for this project has been generously provided by University of Surrey, U.K., Nuffield Foundation, U.K., University of Oulu, Finland, The Finnish Academy, and Aalto University. Networking opportunities through the European collaboration within the COST framework (CM0804, CM1407) is appreciated.