Notizen. Synthesis of (−)-Isohomolavandulol from (+)-Limonene

✍ Scribed by Kula, J. ;Podlejski, J.

• Publisher: John Wiley and Sons
• Year: 1985
• Tongue: English
• Weight: 177 KB
• Volume: 1985
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.198519851017

✦ Synopsis

Synthese von ( -)-Isohomolavandulol aus ( + )-Limonen

Ausgehend von (+)-Limonen wurde (R)-( -)-3-Isopropenyl-6-rnethyl-6-hepten-l-ol (Isohomolavandulol, 6) synthetisiert. Seine spektroskopischen Daten und Geruchs-Charakteristika werdcn angcgeben.

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Wc know only some terpene compounds in which the isoprenoid rule, wanting the combination of two isoprene molecules in a head-to-tail way, has been violated. One of the compounds is (-)-lavandulol found in French lavender oil 'I. The compound is interesting both in regard of its untypical carbon skeleton and its nice odour. That is why so much attention has been paid to its synthesis'! Recently the synthesis of dihydrolavandulol was also reported ' I.

In this paper we present a synthesis of (R)-( -)-3-isopropenyl-6-mcthyl-6-hepten-l-ol (isohomolavandulol, 6) from ( +)-limonene (1). (-)-Isohomolavandulol (6) possesses a nice flower odour similar to lavandulol but a little milder. Its synthesis was realized in accordance to Scheme 1.

Scheme 1 " 8 ' 7

1 ""P

Clcavage of the double bond between C-1 and C-2 in limonene (I) led to formation of the carbon skeleton similar to lavandulol. This kind of transformation of limonene (1) has been reached by its selective ozonolysis in acetic acid. We obtained the keto aldehyde 2