Matsutake alcohol

Acetoxyoctadienes 47 and 48 are suitable starting materials for the synthesis of l-octen-3-ol (Matsutake alcohol) (129), a fragment component of a Japanese mushroom. The synthesis has been accomplished by two methods. In one method, the terminal double bond of 47 was hydro-... 

Trade Names. Matsutake alcohol (Takasago), Morillol (BSAF). 

The synthesis of both enantiomers of matsutake alcohol (a mushroom flavour compound) outlined in the accompanying scheme shows how the sulfinyl group was used to introduce a methylene unit via methylation and regioselective elimination steps [427],... 

The preparation of alkenic alcohols based on rDA processes has found application in the synthesis of natural products. Matsutake alcohol (14a (-)-( )-l-octen-3-ol), an important flavor component of mushrooms, can be prepared in high enantiomeric purity by a method that includes rDA cleavage as a key step. Asymmetric DA addition gave enantiomerically pure adducts that were modified dia-... 

IR-l-0cten-3-ol (Matsutake alcohol). CgH, 0, Mr 128.21, bp. 175 °C, [alg -20.2° LDjo (rat p.o.) 340 mg/kg. A typical mushrooms aroma constituent (olfactory threshold 1 ppb ) with an earthy-fungal odor impact compound in mushroom and Camem-bert flavor (see cheese flavor), but also occurring in many essential oils and flavors, e.g., in lavender, peppermint, rosemary, and thyme oil, as well as seafood flavors. Only the (/ )-enantiomer occurring in 90-97% enantiomeric excess possesses the pure fungus odor, the (S)-compound has a more vegetable-like odor. 

Application Matsutake alcohol (a fragrance compound in a Japanese mushroom) is synthesized by reduction of one terminal double bond by LiAlH4—Cp2TiCl2 after protection of an allylic alcohol group as a diisobutylaluminium alkoxide ... 

Also the secondary telomer, the 3-acetoxy-l,7-octadiene can be a useful starting material. TTie simplest natural product prepared from this telomer is Matsutake alcohol the l-octen-3-ol, a fragrant compound of a Japanese mushroom [9] (Equation 7). 

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