✦ LIBER ✦

A flexible non-amino acid-based formal asymmetric synthesis of naturally occurring (2R,3S)-2-aminotetradeca-5,7-dien-3-ol: observation of a remarkable protecting group effect

✍ Scribed by Bi-Yan He; Tian-Jun Wu; Xian-Yong Yu; Pei-Qiang Huang

Publisher: Elsevier Science
Year: 2003
Tongue: English
Weight: 464 KB
Volume: 14
Category: Article
ISSN: 0957-4166
DOI: 10.1016/s0957-4166(03)00442-7

No coin nor oath required. For personal study only.

✦ Synopsis

A flexible non-amino acid-based formal asymmetric synthesis of naturally occurring antimicrobial (2R,3S)-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.