✦ LIBER ✦

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

✍ Scribed by Kraft, Philip ;Tochtermann, Werner

Publisher: John Wiley and Sons
Year: 1994
Tongue: English
Weight: 377 KB
Volume: 1994
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199419941204

No coin nor oath required. For personal study only.

✦ Synopsis

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‐mediated enolate alkylation and subsequent formation of the cyclic enol ether 8. Ozonolysis and mild chemoselective reduction of the carbonyl function led to the optically active target molecule (+)‐3, which possesses a very interesting clear musk note with elegant sandalwood aspects.

📜 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