1220702-49-7Relevant academic research and scientific papers
Synthesis of optically active tetrahydrozerumbone
Kitayama, Takashi,Ohta, Sayo,Kawai, Yasushi,Nakayama, Tomoyasu,Awata, Masataka
, p. 11 - 15 (2010)
Tetrahydrozerumbone 2, which has a powerful balmy fragrance, has a stereogenic carbon at C2 and can be easily prepared from zerumbone 1, which is one of the most important materials that displays an NMRDOS character. Reduction of 2 gave two diastereomers 3 and 4; their optically active (>99% ee) alcohols were obtained by lipase-catalyzed stereoselective transesterification of each racemic alcohol. The enantioselectivity of tetrahydrozerumbol does not entirely depend on the hydroxyl position but on the 2-methyl position. Compounds (R)-2 and (S)-2 were obtained by Dess-Martin oxidation of the corresponding alcohols. Interestingly, (R)-2 showed a strong balmy fragrance while (S)-2 had hardly any fragrance.
