Practical syntheses of (S)-4-hydroxytetrahydrofuran-2-one, (S)-3-hydroxytetrahydrofuran and their (R)-enantiomers

Liebigs Annales

Volumn , Issue 9, 1997, Pages 1877-1879

  Yuasa, Yoshifumi ^a   Tsuruta, Haruki ^a  

^a TAKASAGO INTERNATIONAL CORPORATION   (Japan)

Author keywords

4 chloro 1,3 butanediol; 4 Chloro 3 hydroxybutanoate; Asymmetric hydrogenation; Cyclizations; Reductions

Indexed keywords

EID: 2142786142     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199719970911     Document Type: Article

References (14)

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8. An example of available material: a component of the HIV aspartyl protease inhibitor KVX-478: R. D. Tung, M. A. Murcko, G. R. Bhisetti (Vertex Pharmaceutical Inc.), WO 9405639, 1994 [Chem. Abstr. 1995, 122, P81141j].
9. M. Kitamura, T. Ohkuma, H. Takaya, R. Noyori, Tetrahedron Lett. 1988, 29, 1555-1556.
10. T. Ikariya, Y. Ishii, H. Kawano, T. Arai, M. Saburi, S. Yoshikawa, S. Akutagawa, J. Chem. Soc., Chem. Commun. 1985, 922-924; [p-toryl-BINAP = 2,2'-bis(di-p-tolylphosphanyl)-1,1′-binaphthyl].
11. + - 18] was recorded in the GC-MS. (The author intends to prepare the acid 6 by an independent route for comparison).
12. The proportion of 8 was determined to be 15% by GC and the structure was identified by comparison with an authentic sample purchased from the Aldrich Chemical Co.
13. r = 35.3 and 37.4 min, in a ratio of 2.8 : 97.2, assignable to the (R,R)- and (R,S)-diastereomer, respectively.
14. With regard to the synthesis of α-butyrolactone, acid cyclizations after basic hydrolysis of esters are known; for example, F. F. Blicke, Jr. W. B. Wright, M. F. Zienty, J. Am. Chem. Soc. 1941, 63, 2488-2490.