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

HRID 2291811Notes

Reaction equation

HRID 2291811 reaction equation
[O:1]=[CH:2][C@@H:3]([C@H]([C@@H]([C@@H](CO)O)O)O)O.[CH3:13][C@@:14]12[C@@H:23](CC[C@@](O)(C=C)C)[C@@:22]([OH:32])([CH3:31])[CH2:21][CH2:20][C@H:19]1[C:18]([CH3:34])([CH3:33])[CH2:17][CH2:16][CH2:15]2>>[OH:32][C:22]1([CH3:31])[CH2:21][CH2:20][CH:19]2[C:18]([CH3:33])([CH2:17][CH2:16][CH2:15][C:14]2([CH3:13])[CH3:23])[CH:34]1[CH2:3][CH2:2][OH:1]

Participants

3

Reactant 2

HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 163263Sclareol2×

Product 1

HCID 91915Decahydro-2-hydroxy-2,5,5,8a-tetramethylnaphthalene-1-ethanol

Procedure

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.]

Workup

  1. additionwas added to each flask
  2. customEach flask was inoculated with 5% by volume of three days
  3. additionwas added in portions during the next 5 days, afterwhich the incubation
  4. waitwas continued for a further 4 days
  5. extractionextracted with ethyl acetate (3×200 mL)
  6. dry with materialdried (Na2SO4)
  7. customEvaporation of the solvent
  8. customprovided a crude
  9. extractionextract (4.0 g), which
  10. customwas crystallized from hexane/chloroform

Sources & evidence

ORD record
ord-3ae9efc6334a48a29e39d32da3206dbc
Source dataset
uspto-grants-1989_01
Patent number
US04798799

Reaction notes

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