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Stereoselective and Enantioselective Syntheses of the Four Stereoisomers of Muscol from (3RS)-Muscone

✍ Scribed by Yoshifumi Yuasa; Haruhiko Fukaya; Yoko Yuasa

Publisher
John Wiley and Sons
Year
2007
Tongue
German
Weight
91 KB
Volume
90
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Two trans stereoisomers of 3‐methylcyclopentadecanol (=muscol), (1__R__,3__R__)‐2 and (1__S__,3__S__)‐2, were efficiently synthesized from (3__RS__)‐3‐methylcyclopentadecanone (=muscone; (3__RS__)‐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, (1__S__,3__R__)‐2 and (1__R__,3__S__)‐2, were obtained by the Mitsunobu inversion of (1__R__,3__R__)‐2 and (1__S__,3__S__)‐2, respectively (Scheme). The absolute configuration of (1__R__,3__R__)‐2 was determined by X‐ray crystal‐structure analysis of its 3‐nitrophthalic acid monoester, 2‐[(1__R__,3__R__)‐3‐methylcyclopentadecyl hydrogen benzene‐1,2‐dicarboxylate ((1__R__,3__R__)‐3b), and by oxidation of (1__R__,3__R__)‐2 to (3__R__)‐muscone.

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