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Volumn 39, Issue 50, 1998, Pages 9229-9232

A conjugate reduction-intramolecular aldol strategy toward the synthesis of pseudolaric acid A

Author keywords

Aldol reactions; Copper and compounds; Natural products

Indexed keywords

ALCOHOL DERIVATIVE; ALDOL; PSEUDOLARIC ACID A; PSEUDOLARIC ACID B; UNCLASSIFIED DRUG;

EID: 0032506682     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02130-3     Document Type: Article
Times cited : (67)

References (24)
  • 8
    • 85038549378 scopus 로고    scopus 로고
    • note
    • 3, KOH, KHMDS) in THF and THF/MeOH from -78°C to 25°C, 6 was the major product. With lithium bases (LDA, LHMDS) at -78°C, the bicyclo[5.5.0] aldol product was formed via the kinetic enolate.
  • 11
    • 85038543857 scopus 로고    scopus 로고
    • note
    • 11. 5 represents any of the diastereomers of 5a
  • 12
    • 85038550446 scopus 로고    scopus 로고
    • note
    • 12. 6 and 7, along with minor amounts of 5b, 5c were obtained in a ratio of about 58:24:12:6.
  • 14
    • 85038545649 scopus 로고    scopus 로고
    • note
    • 23
  • 15
    • 85038542520 scopus 로고    scopus 로고
    • note
    • 24 yielding 9 as a single diastereomer (eq. 6). Reduction of 9 by Raney-Nickel generated 5b. (equation presented)
  • 17
    • 85038543896 scopus 로고    scopus 로고
    • note
    • 16
  • 18
    • 85038540087 scopus 로고    scopus 로고
    • note
    • 18. When excess Stryker's reagent was used, or when the reaction temperature was raised, 6 and 7 also appear as products.
  • 19
    • 85038540970 scopus 로고    scopus 로고
    • note
    • 19. All new compounds were purified and fully characterized by IR, NMR and mass spectral analysis.
  • 20
    • 85038550289 scopus 로고    scopus 로고
    • note
    • 4: 280.1674; Obtained: 280.1672.
  • 21
    • 85038552474 scopus 로고    scopus 로고
    • note
    • 21. Full crystallographic data for the 2,4-dinitrophenylhydrazone derivatives of 5b and 5c can be obtained from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ , UK.
  • 22
    • 85038547605 scopus 로고    scopus 로고
    • note
    • 4: 280.1674; Obtained: 280.1674.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.