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Volumn 61, Issue 12, 1996, Pages 4022-4027

Relative and absolute configuration of allohedycaryol. Enantiospecific total synthesis of its enantiomer

Author keywords

[No Author keywords available]

Indexed keywords

ALLOHEDYCARYOL; GERMACRANOLIDE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0030010598     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9602534     Document Type: Article
Times cited : (37)

References (61)
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    • The fragmentation has also been used for the synthesis of (±)- and (+)-hedycaryol, see: (b) Wharton, P. S.; Sundin, C. E.; Johnson, D. W.; Kluender, H. C. J. Org. Chem. 1972, 37, 34 and (c) Minnaard, A. J.; Wijnberg, J. B. P. A.; de Groot, A. Tetrahedron 1994, 50, 4755, respectively.
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    • The fragmentation has also been used for the synthesis of (±)- and (+)-hedycaryol, see: (b) Wharton, P. S.; Sundin, C. E.; Johnson, D. W.; Kluender, H. C. J. Org. Chem. 1972, 37, 34 and (c) Minnaard, A. J.; Wijnberg, J. B. P. A.; de Groot, A. Tetrahedron 1994, 50, 4755, respectively.
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    • note
    • The numbering system as given in structure 4 will be followed throughout the text of this paper.
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    • For some representative examples, see: (a) Ho, T.-L. Enantioselective Synthesis, Natural Products from Chiral Terpenes; Wiley Interscience: New York, 1992; pp 132-135. (b) Li, Y.; Chen, X.; Shao, S.; Li, T. Synth. Commun. 1993, 23, 2457. (c) Liu, L.; Xiong, Z.; Nan, F.; Li, T.; Li, Y. Bull. Soc. Chim. Belg. 1995, 104, 73.
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    • For some representative examples, see: (a) Ho, T.-L. Enantioselective Synthesis, Natural Products from Chiral Terpenes; Wiley Interscience: New York, 1992; pp 132-135. (b) Li, Y.; Chen, X.; Shao, S.; Li, T. Synth. Commun. 1993, 23, 2457. (c) Liu, L.; Xiong, Z.; Nan, F.; Li, T.; Li, Y. Bull. Soc. Chim. Belg. 1995, 104, 73.
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    • note
    • The use of (S)-(-)-1-phenylethylamine resulted in a selective formation of (-)-10-epi-α-cyperone in 67% overall yield from (+)-dihydrocarvone.
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    • note
    • 2 gave selectively the corresponding α epoxide.
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    • It was expected that ring opening of the side-chain epoxide in 12 would occur during the formation of the allylic selenide. For example, see: Clive, D. L. J. Tetrahedron 1978, 34, 1049.
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    • The epoxidation of olefinic bonds, probably due to the formation of arylperoxyseleninic acid, is a known problem in the selenoxide chemistry, see: (a) Grieco, P. A.; Yokoyama, Y.; Gilman, S.; Nishizawa, M. J. Org. Chem. 1977, 42, 2034. (b) Hori, T.; Sharpless, K. B. J. Org. Chem. 1978, 43, 1689.
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    • The epoxidation of olefinic bonds, probably due to the formation of arylperoxyseleninic acid, is a known problem in the selenoxide chemistry, see: (a) Grieco, P. A.; Yokoyama, Y.; Gilman, S.; Nishizawa, M. J. Org. Chem. 1977, 42, 2034. (b) Hori, T.; Sharpless, K. B. J. Org. Chem. 1978, 43, 1689.
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    • note
    • 28
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    • note
    • We thank Prof. Dr. G. Appendino for supplying copies of the NMR spectra of natural allohedycaryol.
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    • Reference 14, p 636
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    • note
    • 15c,17b
  • 60
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    • note
    • 1H NMR (main peaks) δ 2.49-2.61 (m, 2 H), 3.82 (dd, J = 5.1, 3.6 Hz, 1 H), 5.22-5.52 (m, 2 H), 5.72 (m, 1 H)].
  • 61
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    • note
    • 46 yielded 16 in 95%.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.