P-Chamigrene

P-caryophiyllene Sthujopsene 6a-humulene 7 f-p-tamescne 6 p-chamigrEne 9 cuparerte... 

The biotransformation of spirostructural terpenoids was not carried out. cnt-la-Hydroxy P-chamigrene (367) was inoculated in the same manner as described earlier to give three new metabolites (368-370), of which 370 was the major product (46.2% in isolated yield). The hydroxylation of vinyl methyl group has been known to be very common in the case of microbial and mammalian biotransformation (Furusawa et al., 2005a, 2006) (Figure 20.105). 

FIGURE 20.105 Biotransformation of ewf-la-hydroxy P-chamigrene (367) by Aspergillus niger. 

The liverwort Reboulia hemisphaerica biosynthesizes cyclomyltaylanoids like 362 and also cnt-la-hydroxy-P-chamigrene (367). Biotransformation of cyclomyltayIan-5-ol (362) in the same... 

FIGURE 15.105 Biotransformation of e f-la-hydroxy-p-chamigrene (367) hy Aspergillus niger. 

The spiro compound a-chamigrene has been isolated from Schisandra chinensis fruits and p-chamigrene from Chamaecyparis taiwanensis [27]. p-Chamigrene was the main compound in Trichilia connaroides root oil [35]. 

Guella, G., Mandni, I., Chiasera, G., and Pietra, F. (1990) Rogiolol acetate a novel P-chamigrene-type sesquiterpene isolated from a marine sponge. Helv Chim. Acta. 73,1612-1620. 

The observation that ot- and p-chamigrene are produced in high optical purity (76% and 94—99% optical purities, respectively) in these rearrangements reveals that the ring contraction to the spiro[5.5]undecalyl ring system is essentially irreversible (257, 260). It is remarkable that cuparene is also obtained optically active (25—71% optical purity). Apparently the second ring contraction to the cuparenyl system occurs... 

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