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Volumn 3, Issue 25, 2001, Pages 4075-4078

A Stereoselective synthesis of the C10-C31 (BCDEF ring) portion of pinnatoxin A

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; MARINE TOXIN; PINNATOXIN A; SPIRO COMPOUND;

EID: 0035856898     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0168364     Document Type: Article
Times cited : (31)

References (41)
  • 15
    • 33845185080 scopus 로고
    • For a review on the synthesis of spiroketals, see: Perron, F.; Albizati, K. F. Chem. Rev. 1989, 89, 1617.
    • (1989) Chem. Rev. , vol.89 , pp. 1617
    • Perron, F.1    Albizati, K.F.2
  • 19
    • 0033580904 scopus 로고    scopus 로고
    • For a review on the synthesis of dispiroketals, see: Brimble, M. A.; Farès, F. A. Tetrahedron 1999, 55, 7661.
    • (1999) Tetrahedron , vol.55 , pp. 7661
    • Brimble, M.A.1    Farès, F.A.2
  • 28
    • 0043040097 scopus 로고    scopus 로고
    • note
    • 2, -78 to 0 °C, 93%.
  • 31
    • 0043040095 scopus 로고    scopus 로고
    • note
    • 2O, -78 °C, 80%.
  • 33
    • 0042038458 scopus 로고    scopus 로고
    • note
    • 2O (4:1), 93%.
  • 34
    • 0042538484 scopus 로고    scopus 로고
    • note
    • -1 indicated the existence of a nonconjugated ketone carbonyl.
  • 35
    • 0042037607 scopus 로고    scopus 로고
    • note
    • The ratio of isomers was determined by HPLC analysis (column, Zorbax Sil, 4.6 × 250 mm; eluent. 9% AcOEt in hexane; flow rate, 1.0 mL/min).
  • 36
    • 0042538487 scopus 로고    scopus 로고
    • note
    • Molecular mechanics calculations indicate that the (16S, 19S,23S)-isomer 19 is 2.0 kcal/mol higher in energy than 18.
  • 37
    • 0043040096 scopus 로고    scopus 로고
    • note
    • The other five stereoisomers were estimated to be 3.0-7.6 kcal/ mol higher in energy than 18.
  • 38
    • 0030605819 scopus 로고    scopus 로고
    • In the case of 1,7,9-trioxadispiro[5.1.5.3]hexadecane, the cis-isomer, wherein both O1 and O9 are axially disposed about the central ring, is reported to be less stable by 0.3-0.7 kcal/mol than the trans-isomer without the destabilizing dipole repulsion: McGarvey, G. J.; Stepanian, M. W.; Bressette, A. R.; Ellena, J. F. Tetrahedron Lett. 1996, 37, 5465.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 5465
    • McGarvey, G.J.1    Stepanian, M.W.2    Bressette, A.R.3    Ellena, J.F.4
  • 39
    • 0043039242 scopus 로고    scopus 로고
    • note
    • The ratios of 18, 19, 20, and another unidentified isomer after 4 and 48 h were 85:8:3:4 and 82:8:6:4, respectively.
  • 40
    • 0042539312 scopus 로고    scopus 로고
    • note
    • 4c However, they did not mention the result of epimerization of the desired isomer.
  • 41
    • 0042037608 scopus 로고    scopus 로고
    • note
    • 2O, -78 °C, 73%.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.