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Volumn 5, Issue 11, 2003, Pages 1959-1962

Enantioselective syntheses of cryptocarya triacetate, Cryptocaryolone, and cryptocaryolone diacetate

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; CRYPTOCARYA LATIFOLIA EXTRACT; CRYPTOCARYA TRIACETATE; CRYPTOCARYOLONE; CRYPTOCARYOLONE DIACETATE; PLANT EXTRACT; SORBIC ACID; UNCLASSIFIED DRUG; ACETIC ACID DERIVATIVE; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITOR; ISOENZYME; PROSTAGLANDIN SYNTHASE; PROSTAGLANDIN SYNTHASE INHIBITOR; PYRONE DERIVATIVE;

EID: 0042352244     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0345529     Document Type: Article
Times cited : (71)

References (46)
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    • We have found that for the successful implementation of the Evans acetal-forming reaction, the δ-hydroxy-1-enoates must be in their trans form to prevent lactonization.
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    • As this methodology was being completed, Cossy reported similar cross-metathesis acetyl-protected homoallylic alcohols and enoates; see: (a) BouzBouz, S.; Cossy, J. Org. Lett. 2001, 3, 1451. (b) Cossy, J.; Bargiggia, F.; BouzBouz, S. Org. Lett. 2003, 5, 459. For a related example, see: (c) Dreher, S. D.; Leighton, J. L. J. Am. Chem. Soc. 2001, 123, 341.
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    • As this methodology was being completed, Cossy reported similar cross-metathesis acetyl-protected homoallylic alcohols and enoates; see: (a) BouzBouz, S.; Cossy, J. Org. Lett. 2001, 3, 1451. (b) Cossy, J.; Bargiggia, F.; BouzBouz, S. Org. Lett. 2003, 5, 459. For a related example, see: (c) Dreher, S. D.; Leighton, J. L. J. Am. Chem. Soc. 2001, 123, 341.
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    • 1H NMR analysis (at 500 MHz).
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    • 13C NMR, FTIR, HRMS, and/or elemental analysis.
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    • This result was somewhat surprising given that Grubbs et al. have shown that ω-hydroxy-α-olefins smoothly undergo the cross-coupling reaction with the Weinreb amide of acrylic acid; see ref 19.
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    • For other approaches to pyranone synthesis, see refs 8b and 9d and: (a) Hayakawa, H.; Miyashita, M. Tetrahedron Lett. 2000, 41, 707. (b) Tosaki, S.-Y.; Nemoto, T.; Ohshima, T.; Shibasaki, M. Org. Lett. 2003, 5, 495.
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    • For other approaches to pyranone synthesis, see refs 8b and 9d and: (a) Hayakawa, H.; Miyashita, M. Tetrahedron Lett. 2000, 41, 707. (b) Tosaki, S.-Y.; Nemoto, T.; Ohshima, T.; Shibasaki, M. Org. Lett. 2003, 5, 495.
    • (2003) Org. Lett. , vol.5 , pp. 495
    • Tosaki, S.-Y.1    Nemoto, T.2    Ohshima, T.3    Shibasaki, M.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.