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A Short Synthesis of (±)-Muscone

✍ Scribed by Valentin Rautenstrauch; Roger L. Snowden; Simon M. Linder

Publisher
John Wiley and Sons
Year
1990
Tongue
German
Weight
412 KB
Volume
73
Category
Article
ISSN
0018-019X

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✦ Synopsis

Introduction.

-Muscone (l), a perfumistically important macrocyclic ketone, has attracted considerable synthetic interest over the past sixty years'). An attractive approach is the three-C-atom ring-expansion concept developed in Firmenich research laboratories and which involves cleavage of a cyclopentacyclododecene system constructed from cyclododecanone [3]. We now present a short synthesis of (&)-l which represents an extension of this strategy.

Results and Discussion. -The synthesis of 1 ( c j Scheme I ) starts by treatment of 2-(2'-methylprop-2'-enyl)cyclododecan-1 -one (2) with Me,AlCI (1.3 mol-equiv.)') in 1,2-dichloroethane/hexane at 70" during 8 h followed by an aqueous basic workup. Scheme 1 2 3 (Z)-11 1 (muscone) i) Me2AIC1, 1,2-dichloroethane/hexane, 70°, then aq. NaOH soln. ii) KH, HMPA, 120", then aq. NH,C1 soln. iii) H?, 5 % Pd/C, cyclohexane. ') ' ) For a review of muscone syntheses prior to 1979-1980, see [l]; for more recent syntheses, see [2] [3d,e]. Other alkylaluminium halides gave inferior results. For example, Et,AICI afforded 3 in much lower yidd (5-10%) producing substantial amounts (40-50%) of 2-(2'-methylprop-2'-enyl)cyclodudecan-l-ol (i) (1.3 : 1 & i diastereoisomeric mixture) via reduction of 2. Data oji. Major Isomer: colourless oil. B. p.

(bulb-to-bulb dist.) 170-180"/0.02 Torr. Rf (cyclohexane/AcOEt 9 :1) 0.30. IR(CDC1,):

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