Deceased on October 19, 1997.
About a Practical Synthesis of Ambrox® from Sclareol: a New Preparation of a Ketone Key Intermediate and a Close Look at its Baeyer–Villiger Oxidation
Version of Record online: 21 OCT 2004
Copyright © 2004 Schweizerische Chemische Gesellschaft, Switzerland
Helvetica Chimica Acta
Volume 87, Issue 10, pages 2695–2705, October 2004
How to Cite
Moulines, J., Bats, J.-P., Lamidey, A.-M. and Da Silva, N. (2004), About a Practical Synthesis of Ambrox® from Sclareol: a New Preparation of a Ketone Key Intermediate and a Close Look at its Baeyer–Villiger Oxidation. HCA, 87: 2695–2705. doi: 10.1002/hlca.200490239
- Issue online: 21 OCT 2004
- Version of Record online: 21 OCT 2004
- Manuscript Received: 1 JUN 2004
The latest route to Ambrox® (1) starting from sclareol (2) proceeds through an oxy ketone 4 (Scheme 1). A new practical synthesis of the key intermediate 4 is described; it is equivalent to a partial oxidative degradation of sclareol (2) with peracetic and periodic acids (Scheme 2). The final product of the BaeyerVilliger oxidation of the oxy ketone 4 with commercial peracetic acid is decisively dependent on the reaction conditions because the expected acetate 9 reacts with any nucleophile, especially the peracid (Scheme 3). Furthermore, this acetate 9 is very prone to eliminative coupling (Scheme 4).