Abstract
A flexible non-amino acid-based formal asymmetric synthesis of naturally occurring antimicrobial (2 R,3 S)-2-aminotetradeca-5,7-dien-3-ol is reported. The method features a flexible and highly regioselective Grignard addition to ( S)-malimide followed by a trans-diastereoselective reductive deoxygenation. The scope and limitations of the highly regio and diastereoselective reductive alkylation of malimides were defined. A remarkable protecting group effect on the regio and diastereoselective reductive alkylation of malimides was observed.
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