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Volumn 71, Issue 4, 2006, Pages 1416-1429

Synthesis of the proposed structure of mucoxin via regio- and stereoselective tetrahydrofuran ring-forming strategies

Author keywords

[No Author keywords available]

Indexed keywords

ANTITUMOR AGENT; NATURAL PRODUCT; SYNTHETIC MATERIAL; THF RING-FORMING REACTIONS;

EID: 33644560625     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052073c     Document Type: Article
Times cited : (54)

References (79)
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    • Cutler, S. J., Cutler, H. G., Eds.; CRC Press: Boca Raton, FL
    • Johnson, H. A.; Oberlies, N. H.; Alali, F. Q.; McLaughlin, J. L. Thwarting resistance: Annonaceous acetogenins as new pesticidal and antitumor agents. In Biologically Active Natural Products; Cutler, S. J., Cutler, H. G., Eds.; CRC Press: Boca Raton, FL, 2000: pp 173-183.
    • (2000) Biologically Active Natural Products , pp. 173-183
    • Johnson, H.A.1    Oberlies, N.H.2    Alali, F.Q.3    McLaughlin, J.L.4
  • 34
    • 0002928569 scopus 로고    scopus 로고
    • Asymmetric epoxidation of unfunctionalized olefins and related reactions
    • Ojima, I., Ed.; Wiley-VCH: New York
    • Katsuki, T. Asymmetric Epoxidation of Unfunctionalized Olefins and Related Reactions. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; pp 287-325.
    • (2000) Catalytic Asymmetric Synthesis, 2nd Ed. , pp. 287-325
    • Katsuki, T.1
  • 72
    • 0000432226 scopus 로고    scopus 로고
    • Catalytic asymmetric dihydroxylation-discovery and development
    • Ojima, I., Ed.; Wiley-VCH: New York
    • Johnson, R. A.; Sharpless, K. B. Catalytic asymmetric dihydroxylation-discovery and development. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; pp 357-398.
    • (2000) Catalytic Asymmetric Synthesis, 2nd Ed. , pp. 357-398
    • Johnson, R.A.1    Sharpless, K.B.2
  • 76
    • 0002041453 scopus 로고    scopus 로고
    • Catalytic asymmetric epoxidation of allylic alcohols
    • Ojima, I., Ed.; Wiley-VCH: New York
    • Johnson, R. A.; Sharpless, K. B. Catalytic asymmetric epoxidation of allylic alcohols. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; pp 231-280.
    • (2000) Catalytic Asymmetric Synthesis, 2nd Ed. , pp. 231-280
    • Johnson, R.A.1    Sharpless, K.B.2
  • 77
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    • note
    • Vicinal protons on substituted THF rings often do give rise to nOe's regardless of their relative geometries. Therefore, the presence of a strong nOe between H13 and H14 does not conclusively establish the cis configuration of substituents at C13 and C14. However, stereochemistry at C13/C14 arises from the SAD reaction of a trans-olefin, which must yield a trans-epoxide. Although it is very unlikely that the undesired diastereomer is obtained during the asymmetric epoxidation, to allow for that possibility, the relationship between H16 and H13 would have to be necessarily cis after cyclization to the tetrahydrofuran ring (note that the retention of stereochemistry during the cyclization reaction has been clearly demonstrated in ref 20). Because the trans stereochemistry is clearly established between H13 and H16, the assigned and expected cis relationship between H13 and H14 is further supported.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.