Highly stereoselective preparation of (3R,4S)-3,4-chromanediol by deracemization of (±)-3-hydroxy-4-chromanone by Trichosporon cutaneum

Tetrahedron Asymmetry

Volumn 16, Issue 15, 2005, Pages 2515-2519

  Lunardi, Inês ^a   Conceição, Gelson J A ^b   Moran, Paulo J S ^a   Rodrigues, J Augusto R ^a  

^a UNIVERSITY OF CAMPINAS   (Brazil)

^b UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

4 CHROMANONE DERIVATIVE;

ANIMAL CELL; ARTICLE; ENANTIOMER; NONHUMAN; PRIORITY JOURNAL; RACEMIZATION; REDUCTION; STEREOCHEMISTRY; TRICHOSPORON CUTANEUM; YEAST;

EID: 23644435762     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2005.06.020     Document Type: Article

References (20)

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14. R.M. Moriarty, O. Prakash, and C.T. Thachet Synth. Commun. 1984 1373
15. Typical procedure: To a slurry of 3 g (wet weight) of Trichosporon cutaneum CCT 1903 and glucose (1 g) in different phosphate buffers (50 mL), a solution of (±)-2 (50 mg) in ethanol (0.5 mL) was added. Experiments were also performed in different phosphate buffers (50 mL) in the absence of glucose. The resulting suspensions were stirred on an orbital shaker (150 rpm) at 28°C until complete consumption of 2. After centrifugation, the supernatants were thoroughly extracted with ethyl acetate. Purification of the crude product was achieved by flash column chromatography on silica gel, using hexane/ethyl acetate (2:1 and 1:1) as eluent.
16. This strain is stored at 'André Tosello' Research Foundation (Brazil). Synonym Trichosporon beigelli (Kuechenmeister & Rabenhorst) Vuillemin. It was cultivated in 2% SDB (Sabouraud dextrose broth, 1 L) for 2-3 days incubation at 28°C on an orbital shaker (150 rpm) before use. The cells were harvested by centrifugation (5000 rpm).
17. 3: 166.06299.
18. The ee of diol 3 was determined by GC-MS (Shimadzu QP-5000) analysis through a Chirasil-dex capillary chiral column (30 m × 0.25 mm × 0.25 μm), after isolation by flash column chromatography (vide supra Ref. 11) and conversion to the corresponding acetonide derivative.
19. +•, 31%), 148 (1%), 131 (3%), 120 (86%), 121 (100%), 104 (14%), 91 (9%), 77 (14%), 65 (11%), 51 (8%).
20. The spectroscopic data of this compound were identical to those reported previously: M.G. Constantino, V. Lacerda, and G.V.J. da Silva J. Heterocycl. Chem. 40 2003 369