Hydroximate as a synthetically useful functional group part II: Synthesis of (±)-oxo-parabenzlactone

Chemical and Pharmaceutical Bulletin

Volumn 44, Issue 6, 1996, Pages 1285-1287

  Miyata, Okiko ^a   Nishiguchi, Atsuko ^a   Ninomiya, Ichiya ^a   Naito, Takeaki ^a  

^a KOBE PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

hydroximate; oxo parabenzlactone; thiophenol, lignan; thiyl radical cyclization

Indexed keywords

LACTONE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0029943841     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.44.1285     Document Type: Article

References (15)

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9. Radical cyclization of the allyl esters is known to proceed to give the 2,3-disubstituted butyrolactones in low yield. a) Belletire J. L., Mahmoodi N. O., Tetrahedron Lett., 30, 4363-4366 (1989). b) Belletire J. L., Mahmoodi N. O., J. Nat. Prod., 55, 194-206 (1992).
10. Radical cyclization of the allyl esters is known to proceed to give the 2,3-disubstituted butyrolactones in low yield. a) Belletire J. L., Mahmoodi N. O., Tetrahedron Lett., 30, 4363-4366 (1989). b) Belletire J. L., Mahmoodi N. O., J. Nat. Prod., 55, 194-206 (1992).
11. According to the reported procedure, the Z-dienylhydroximate 2 was prepared from the acid chloride via the the corresponding hydroxamate without formation of the E-isomer. Johnson J. E., Springfield J. R., Hwang J. S., Hayes L. J., Cunningham W. C., McClaugherty D. L., J. Org. Chem., 36, 284-294 (1971).
12. a) Naito T., Honda Y., Miyata O., Ninomiya I., J. Chem. Soc., Perkin Trans. 1, 1995, 19-26.
13. b) Sato T., Wada Y., Nishimoto M., Ishibashi H., Ikeda M., J. Chem. Soc., Perkin Trans 1, 1989, 879-886.
14. Moriarty R. M., Vaid R. K., Koser G. F., Synlett, 1990, 365-383.
15. As a preliminary experiment, we have found that treatment of the cis- and trans-hydroximates 10 with 3 equiv. of [hydroxy(tosyloxy)iodo] benzene gave the cis- and trans-lactones 11 having a sulfinyl group in 77-79% yield.