A short synthesis of optically active corey lactone by means of the dirhodium(II)-catalyzed intramolecular C-H insertion reaction of an α-diazo ketone

Synthesis

Volumn , Issue 7, 1998, Pages 973-974

  Yakura, Takayuki ^a   Yamada, Seiji ^a   Azuma, Miki ^a   Ueki, Akiharu ^a   Ikeda, Masazumi ^a  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

2 oxocyclopentanecarboxylate; Corey lactone; Dirhodium(II) tetraacetate; Dirhodium(II) catalyzed intramolecular C H insertion; diazo ketone

Indexed keywords

KETONE DERIVATIVE; LACTONE DERIVATIVE; RHODIUM;

ARTICLE; CATALYSIS; MOLECULAR DYNAMICS; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 0031825110     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-2095     Document Type: Article

References (18)

1. Corey, E. J.; Weinshenker, N. M.; Schaaf, T. K.; Huber, W. J. Am. Chem. Soc. 1969, 91, 5675.
2. Corey, E. J.; Schaaf, T. K.; Huber, W.; Koelliker, U.; Weinshenker, N. M. J. Am. Chem. Soc. 1970, 92, 397.
3. Corey, E. J.; Shirahama, H.; Yamamoto, H.; Terashima, S.; Venkateswarlu, A.; Schaaf, T. K. J. Am. Chem. Soc. 1971, 93, 1490.
4. Corey, E. J.; Albonico, S. M.; Koelliker, U.; Schaaf, T. K.; Varma, R. K. J. Am. Chem. Soc. 1971, 93, 1491.
5. For reviews, see: Roberts, S. M.; Scheinmann, F. New Synthetic Routes to Prostaglandins and Thromboxanes; Academic Press: 1982.
6. Collins, P. W.; Djuric, S. W. Chem. Rev. 1993, 93, 1533.
7. A recent report on the synthesis of the optically active Corey lactone: Node, M.; Nakamura, D.; Nishide, K.; Inoue, T. Heterecycles 1997, 46, 535, and references cited therein.
8. Yakura, T.; Yamada, S.; Kunimune, Y.; Ueki, A.; Ikeda, M. J. Chem. Soc., Perkin Trans. 1 1997, 3643.
9. Yakura, T.; Yamada, S.; Ueki, A.; Ikeda, M. Synlett 1997, 185.
10. Taber, D. F.; Song, Y. J. Org. Chem. 1997, 62, 6603.
11. Taber, D. F.; You, K. K.; Rheingold, A. L. J. Am. Chem. Soc. 1996, 118, 547, and references cited therein.
12. For recent reviews of Rh(II)-catalyzed reactions, see: Doyle, M. P. Aldrichimica Acta 1996, 29, 3.
13. Hashimoto, S.; Watanabe, N.; Anada, M.; Ikegami, S. J. Synth. Org. Chem., Jpn. 1996, 54, 988.
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15. Holmquist, C. R.; Roskamp, E. J. J. Org. Chem. 1989, 54, 3258.
16. In practice, it is not necessary to separate the two isomers 3 and 4 at this stage. The mixture of 3 and 4 was converted into 8 in 18% overall yield from α-diazo ketone 2. The oxidation of the (2S,3S,4S)-isomer of 7 derived from 4 gave the corresponding carboxylic acid which could be easily removed by washing with a weak base solution.
17. Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936.
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