Abstract
A (2E,4E)-7-hydroxy-2,4-dienoic acid, previously employed as a key intermediate for the total synthesis of the macrodiolide antibiotic elaiolide, was prepared stereoselectively and concisely from (S)-2-methyl-3-trityloxypropanal by a three-step sequence consisting of Brown's asymmetric crotylboration, olefin cross-metathesis, and alkaline treatment. Ethyl 3-pivaloyloxy-4-pentenoate was used as a masked dienoate in the cross-metathesis step.
Original language | English |
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Pages (from-to) | 3163-3166 |
Number of pages | 4 |
Journal | Tetrahedron Letters |
Volume | 48 |
Issue number | 18 |
DOIs | |
Publication status | Published - 2007 Apr 30 |
Keywords
- 2,4-Alkadienoic acid
- Antibiotic
- Cross-metathesis
- Elaiolide
- Enantioselective synthesis
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry