Synthesis of drim

Enzell. Tobacco chemistry. Structure and synthesis of drim-8-en-7-one, a new tobacco constituent. Acta Chem Scand SerB 1975 29 51. NT377... 

It is necessary also to note that the diol (41) has been used as a starting compound for the synthesis of drim-9(ll)-en-8a-ol (80), one of the two C-8 epimeric metabolites of the fungus Aspergillus oryzae [59], used in Japan in baking and in manufacturing of some beverages (sake and others). On tosylation, the diol (41) afforded the monotosylate (81) which was transformed to the unsaturated alcohol (80) on treatment with Nal and Zn [60] (Scheme 12). 

Synthesis of Drim-7fi 8/5,9a-triol from Drim-8-en-7-one Polyhydroxylated drimanes are of interest as potentially biologically... 

We carried out the synthesis of drim-7P,8p,9a-triol (149) starting with drim-8-en-7-one (27) [95]. The latter was epoxidised to the epoxy ketone (150), which was reduced to the epoxy alcohol (151), whose acetate (152) was transformed, on interaction with HC104, to a mixture of the triol (149) (41% yield) and its monoacetate (153) (54%). Compound (153) gives the triol (149) on saponification, and vice versa, the triol (149) is quantitatively acetylated to the monoacetate (153). The triol (149) forms the acetonide (154). That conversion proves its absolute configuration at C-8 and C-9, confirmed by spectral data. 

We carried out a three-step synthesis of the keto acetate (31) from drim-8-en-7-one (27) in the overall yield of 66.5% [82] (Scheme 20). The ketone (27) was enolacetylated to the diene acetate (119), whose oxidation with MPPA gave the keto alcohol (120), acetylated to the keto acetate (31). It should be noted that the structure of the keto alcohol (120) was determined not only on the basis of spectral data, but also was confirmed by X-ray [83],... 

We carried out a short and efficient synthesis of trans-tetrahydroactinidiolide (155) from drim-8-en-7-one (27) [105]. On exhaustive ozonolysis of drim-8-en-7-one (27) and subsequent treatment of resulting products with hydrogen peroxide, the keto acid (157) was obtained in a quantitative yield. 

Drim-8-en-l 1-oic acid (158) is a convenient synthon for the preparation of polyfunctional drimanes. This acid has been used as an intermediate in the total synthesis of 1,6,7-tridesoxyforskolin (159), a related compound to forskolin (160), possessing ionotropic, antihypotensive and other activities [106]. Optically active compound (159) was isolated together with forskolin from the plant Coleus forskohlii [107]. 

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