Abstract
The enantioselective total synthesis of (-)-stemoamide using Overman/Claisen rearrangement of an allylic 1,2-diol is reported. The enantiopure allylic 1,2-diol was efficiently prepared from naturally occurring dimethyl tartrate. The chirality transfer reactions through two consecutive [3,3]-sigmatropic rearrangements proceeded with complete diastereoselectivity in a one-pot process.
Original language | English |
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Article number | ss-2016-c0050-st |
Pages (from-to) | 1647-1654 |
Number of pages | 8 |
Journal | Synthesis (Germany) |
Volume | 48 |
Issue number | 11 |
DOIs | |
Publication status | Published - 2016 Jun 2 |
Keywords
- alkaloid
- allylic compound
- diol
- sigmatropic rearrangement
- total synthesis
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry