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ChemInform Abstract: Synthesis of Medium and Large Ring Compounds. Part 39. Stereoselective Synthesis of Both Enantiomers of 13-Tetradecanolide by Ring Enlargement with Different Chiral Building Blocks and Olfactory Comparison with (12R)-(+)- and (12S)-(-)-12-Methyl-13-tridecanolide.

✍ Scribed by P. KRAFT; W. TOCHTERMANN

Book ID
112023822
Publisher
John Wiley and Sons
Year
2010
Weight
33 KB
Volume
26
Category
Article
ISSN
0931-7597

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📜 SIMILAR VOLUMES

Synthesis of medium and large ring compo
Synthesis of medium and large ring compounds, XXXIX. Stereoselective synthesis of both enantiomers of 13-tetradecanolide by ring enlargement with different chiral building blocks and olfactory comparison with (12R)-(+)- and (12S)-(−)-12-methyl-13-tridecanolide
✍ Kraft, Philip ;Tochtermann, Werner 📂 Article 📅 1995 🏛 John Wiley and Sons 🌐 English ⚖ 712 KB

## 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

Synthesis of Medium and Large Ring Compo
Synthesis of Medium and Large Ring Compounds, XXXVIII. Ring Enlargement of Cyclodecanone by a Chiral Building Block: Synthesis and Olfactory Properties of (12R)-(+)-12-Methyl-13-Tridecanolide
✍ Kraft, Philip ;Tochtermann, Werner 📂 Article 📅 1994 🏛 John Wiley and Sons 🌐 English ⚖ 377 KB

## 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