ChemInform Abstract: Synthesis of Medium and Large Ring Compounds. Part 40. Ring Enlargement by Alkylated 3-Hydroxybutyrates: A Synthesis of (12S,13R)-( -)-12-Methyl-13-tetradecanolide.
✍ Scribed by P. KRAFT; W. TOCHTERMANN
- Book ID
- 112025758
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 34 KB
- Volume
- 27
- Category
- Article
- ISSN
- 0931-7597
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## Abstract Starting from a cycloalkanone and the chiral building blocks 2 or 3 both enantiomers of 13‐tetradecanolide (1, n = 14) were prepared by ring‐enlargement reactions. Cycloundeca‐none (4) was α‐alkylated with the protected hydroxy halide 2 derived from (__S__)‐(−)‐methyl lactate. Acid‐cata
## Abstract The title compound (+)‐3 was synthesized in four steps by ring enlargement of cyclodecanone (6) with the chiral building block 5. The protected hydroxy halide 5, easily prepared from commercially available (2__S__)‐(+)‐methyl 3‐hydroxy‐2‐methylpropanoate (4), was introduced by HMPA‐medi