(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal → Decahydro-2-hydroxy-2,5,5,8a-tetramethylnaphthalene-1-ethanol

Participants

Reaction Steps

Four flasks, each containing an aqueous solution (100 mL) of 0.1% NH4NO3, 0.1% H2KPO4, 0.05% MgSO4.7H2O, trace minerals, and Vitamin B complex were sterilized at 120° C. for 20 minutes. A 50% aqueous solution of dextrose (5 mL) and Tween-80 (0.1 mL), containing Sclareol (4) (10 mg) was added to each flask. Each flask was inoculated with 5% by volume of three days grown cells CBS 214.83 (ATCC 20624). The cultures were then incubated at 25±1° C. on a rotary shaker (200 rpm) for 3 to 4 days. After the initial incubation period a mixture of Sclareol dissolved in Tween-80 (8.0 g) was added in portions during the next 5 days, afterwhich the incubation was continued for a further 4 days. At the end of the incubation period the contents of the four flasks were combined, extracted with ethyl acetate (3×200 mL) and dried (Na2SO4). Evaporation of the solvent provided a crude extract (4.0 g), which was crystallized from hexane/chloroform to provide decahydro-2-hydroxy-2,5,5,8a-tetramethylnaphthaleneethanol (3) (2.4 g), mp 130.5°-131.5° C., (lit. 132°-133° C.) GLC purity 100%, H-NMR (CDCl3) δ0.79 (6H, 2s), 0.87 (3H, 2), (3H, 2), 0.9-20 (16H, m), 3.41-3.49 (1H, m), 3.72-3.79 (1H, m). IR (CHCl3) νmax, 3580, 3360, 2950, 1460, 1380 cm. MS m/e 236, 221, 117, 137, 109. [α]22D =-16.8° (CHCl3). [Literature 132°-133° C., [α]D22.5 =-17.3° (CHCl3).] [See M. Stoll and M. Hinder Helv. Chim. Acta (1953) 36 1955-2008.]

Provenance & Evidence