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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Journal | Synthesis (Germany) |
DOIs | |
Publication status | Accepted/In press - 2016 Feb 23 |
Keywords
- alkaloid
- allylic compound
- diol
- sigmatropic rearrangement
- total synthesis
ASJC Scopus subject areas
- Organic Chemistry
- Catalysis