A Catalytic Asymmetric Synthesis of 11-Deoxy-PGF1α Using ALB, a Heterobimetallic Multifunctional Asymmetric Complex

Journal of Organic Chemistry

Volumn 63, Issue 11, 1998, Pages 3666-3672

  Yamada, Ken Ichi ^a   Arai, Takayoshi ^a,b   Sasai, Hiroaki ^a,b   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000429727     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9723319     Document Type: Article

References (33)

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9. 1α, see; (a) Caton, M. P. L.; Coffee, E. C. J.; Watkins, G. L. Tetrahedron Lett. 1972, 773. (b) Alvarez, F. S.; Wren, D.; Prince, A. J. Am. Chem. Soc. 1972, 94, 7823. (c) Alvarez, F. S.; Wren, D. Tetrahedron Lett. 1973, 569. (d) Burton, T. S.; Caton, M. P. L.; Coffee, E. C. J.; Parker, T.; Stuttle, K. A. J.; Watkins, G. L. J. Chem. Soc., Perkin Trans, l 1976, 2550.
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13. As expected, the use of dibenzyl malonate instead of dibenzyl methylmalonate (4) as a Michael donor gave the three-component coupling products in only 9% yield.
14. 1H NMR. chemical equation presented.
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32. The optical purity of 21 was determined after converting it to a-alcohol ii, shown below, by chiral stationary-phase HPLC analysis (DAICEL CHIRALPAK AD, 5% i-PrOH-hexane, flow rate: 1.0 mL/ min, retention time: 25 min ii and 29 min its enantiomer, detection at 254 nm). chemical equation presented.
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