Caryophyllene Botrytis cinerea

An illustration of the plethora of reactions that may occur is afforded by the transformation of caryophyllene oxide by Botrytis cinerea. Although most of the reactions were hydrox-ylations or epoxidations, two involved transannular reactions (a) between the C4-epoxide oxygen and Cy and (b) between the C4-epoxide and C13 with formation of a caryolane (Figure 7.47) (Duran et al. 1999). 

FIGURE 7.47 Transformation of caryophyllene oxide by Botrytis cinerea. 

Duran R, E Corrales, R Hemandez-Galan, IG Collado (1999) Biotransformation of caryophyllene oxide by Botrytis cinerea. J Nat Prod 62 41-44. 

FIGURE 20.134 Biotransformation of (-)-P-caryophyllene epoxide (453) by Botrytis cinerea. 

Cgl-acetate and [4,5- - evalonate by Botrytis cinerea has shown that famesyl pyrophosphate is folded as in (25), The initial oyclization is similar to that vAiich leads to caryophyllene. Examination of the deuterium ... 

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