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Preparative bioorganic chemistry, XV. Preparation of optically pure 2,4,4‐trimethyl‐2‐cyclohexen‐1‐ol, a new and versatile chiral building block in terpene synthesis
Author(s) -
Mori Kenji,
Puapoomchareon Prapai
Publication year - 1991
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1991199101182
Subject(s) - chemistry , terpene , bioorganic chemistry , organic chemistry , block (permutation group theory) , optically active , combinatorial chemistry , geometry , mathematics , enzyme
Enzymatic hydrolysis of (±)‐2,4,4‐trimethyl‐2‐cyclohexenyl acetate [(±)‐ 3 ] with pig liver esterase yielded ( R )‐(+)‐2,4,4‐trimethyl‐2‐cyclohexen‐1‐ol [( R )‐ 2 ] and unchanged ( S )‐(−)‐acetate ( S )‐ 3 . Enantiomerically pure ( S )‐ 2 was converted into ( R )‐dihydro‐α‐ionone ( 10 ).