Abstract
AbstractTwo trans stereoisomers of 3‐methylcyclopentadecanol (=muscol), (1R,3R)‐2 and (1S,3S)‐2, were efficiently synthesized from (3RS)‐3‐methylcyclopentadecanone (=muscone; (3RS)‐1) by a highly stereoselective reduction (Scheme). L‐Selectride® (=lithium tri(sec‐butyl)borohydride) was used, followed by the enantiomer resolution by lipase QLG (Alcaligenes sp.). The cis stereoisomers of muscol, (1S,3R)‐2 and (1R,3S)‐2, were obtained by the Mitsunobu inversion of (1R,3R)‐2 and (1S,3S)‐2, respectively (Scheme). The absolute configuration of (1R,3R)‐2 was determined by X‐ray crystal‐structure analysis of its 3‐nitrophthalic acid monoester, 2‐[(1R,3R)‐3‐methylcyclopentadecyl hydrogen benzene‐1,2‐dicarboxylate ((1R,3R)‐3b), and by oxidation of (1R,3R)‐2 to (3R)‐muscone.
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