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Synthesis of (R)- and (R)-4-methyl-6-2′-methylprop-1′-enyl-5,6-dihydro-2H-pyran (Nerol oxide) and Natural Occurrence of its Racemate

✍ Scribed by Günther Ohloff; Wolfgang Giersch; Karl H. Schulte-Elte; Paul Enggist; Edouard Demole

Publisher
John Wiley and Sons
Year
1980
Tongue
German
Weight
467 KB
Volume
63
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Following a known procedure, a mixture of (−)‐(2__S__,3__R__)‐ and (+)‐(2__R__,3__R__)‐2,3‐epoxy‐citronellols (5) was prepared from (−)‐(R)‐linalool (3) via epoxy alcohol 4 and then reduced to (−)‐(R)‐3‐hydroxy‐citronellol (6). Sensitized photooxygenation of (−)‐(R)‐diol 6 led in part to (−)‐(R)‐triol 8 which was cyclodehydrated by dilute acid to a mixture of diastereoisomeric tetrahydropyran‐4‐ols 9 and 10. Dehydration of hydroxy ethers 9 and 10 afforded (−)‐(S)‐nerol oxide (11) and (+)‐(R)‐nerol oxide (12), respectively, with an optical purity of 91%. Nerol oxide isolated from Bulgarian rose oil (0.038%) proved to be racemic. These results shed some light on the formation of nerol oxide in plants.

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