2.6- Dimethyl-2,6-octadiene-l,8-diol

Oxidation of 1,5-dienes to c -tetiahydrofurandiols was accomplished with RuO /aq. Na(10 )/acetone-EtOAc thus 2,5-dimethyl-1,5-hexadiene gave tetrahydrofurandiol, geranyl acetate yielded cw-tetrahydrofurandiol, and trans, tra 5-2,6-dimethyl-2,6-octadiene-l,8-diol diacetate (1) gave tetrahydrofuran ketol diacetate (2) (Fig. 3.12 cf. mech. Ch. 1) [174],... 

Fig. 3.12 Oxidation by RuO of 2,6-dimethyl-2,6-octadiene-l,8-diol diacetate (1) to tetrahydrofuran ketol diacetate (2) [174]...

The most important metabolites from geraniol (271), nerol (272), and citronellol (258) are summarized in Figure 19.9. In the same year, the biotransformation of these monoterpenes by B. cinerea in model solutions was described by another group (Rapp and Mandery, 1988). Although the major metabolites found were co-hydroxylation compounds, it is important to note that some new compounds that were not described by the previous group were detected (Figure 19.9). Geraniol (271) was mainly transformed to (2 , 5 )-3,7-dimethyl-2,5-octadiene-l,7-diol (318), (B)-3,7-dimethyl-2,7-octadiene-l,6-diol (319), and (2 , 6 )-2,6-dimethyl-2,6-octadiene-l,8-diol (300) and nerol (272) to (2Z,5 )-3,7-dimethyl-2,5-octadiene-l,7-diol (314), ( -3,7-dimethyl-2,7-octadiene-l,6-diol (315),... 

A. niger isolated from garden soil biotransformed linalool and its acetates to give linalool (206), 2,6-dimethyl-2,7-octadiene-l,6-diol (8-hydroxylinalool (219a), a-terpineol (34), geraniol (271), and some unidenti ed products in trace amounts (Madyastha and Krishna Murthy, 1988a,b). 

Figure 5.1a (1) cis and trans linalool oxide (5-ethenyltetrahydro-a,a,5-trirnethyl-2-furanmethanol) (furanic form) (2) linalool (3,7-dimethyl-l,6-octadien-3-ol) (3) a-terpineol (a,a,4-trimethyl-3-cycloexene-l-methanol) (4) (Z,E) ocimenol (2,6-dimethyl-5,7-octen-2-ol) (5) cis and trans linalool oxide (pyranic form) (6) citronellol (3,7-dimethyl-6-octen-l-ol) (7) nerol (Z), geraniol (E) (3,7-di-methyl-2,6-octadien-l-ol) (8) Ho-diendiol I (3,7-dimethyl-l,5-octadiene-3,7-diol) (9) endiol (3,7-dimethyl-l-octene-3,7-diol) (10) Ho-diendiol II (3,7-dimethyl-l,7-... 

Figure 5.1a (Continued) octadiene-3,6-diol) (11) hydroxycitronellol (3,7-di methyloctane-l,7-diol) (12) 8-hydroxydihydrolinalool (2,6-dimethyl-7-octene-l,6-diol) (13) 7-hydroxygeraniol (E-3,6-dimethyl-2-octene-l,7-diol) (14) 7-hydro-xynerol (Z-3,6-dimethyl-2-octene-l, 7-diol) (15) cis and trans 8-hydroxy linalool (E- and Z-2,6-dimethyl-2,7-octadiene-l,6-diol) (16) p-menthenediol I (p-menth-l-ene-7,8-diol) (17) E-geranic acid (3,7-dimethyl-2,6-octadienoic acid) (18) E-2,6-dimethyl-6-hydroxyocta-2,7-dienoic acid (19) E- and Z-sobrerol or p-menthenediol II (p-menth-l-ene-6,8-diol) (20) cis and trans rose oxide (21) nerol oxide (22) 2-exo-hydroxy-1,8-cineol (23) 1,8-cineol (24) wine lactone (25) cis and trans 1,8-terpin (26) triol (2,6-dimethyloctane-2,3,6-triol) (27) hotrienol [(5E)-3,5-dimethylocta-l,5,7-trien-3-ol] (28) myrcenol (2-methyl-6-methylene-7-octen-2-ol)...

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