171963-67-0Relevant academic research and scientific papers
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
Moulines, Jean,Bats, Jean-Paul,Lamidey, Anne-Marie,Da Silva, Nicole
, p. 2695 - 2705 (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 Baeyer - Villiger 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).
