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
- 17 September 1980
- journal article
- research article
- Published by Wiley in Helvetica Chimica Acta
- Vol. 63 (6) , 1582-1588
- https://doi.org/10.1002/hlca.19800630626
Abstract
Following a known procedure, a mixture of (−)‐(2S,3R)‐ and (+)‐(2R,3R)‐2,3‐epoxy‐citronellols (5) was prepared from (−)‐(R)‐linalool (3)viaepoxy alcohol4and then reduced to (−)‐(R)‐3‐hydroxy‐citronellol (6). Sensitized photooxygenation of (−)‐(R)‐diol6led in part to (−)‐(R)‐triol8which was cyclodehydrated by dilute acid to a mixture of diastereoisomeric tetrahydropyran‐4‐ols9and10. Dehydration of hydroxy ethers9and10afforded (−)‐(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.This publication has 13 references indexed in Scilit:
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