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Volumn 12, Issue 10, 2010, Pages 2342-2345

Enantioselective synthesis of α-methylene-β-hydroxy carboxylic acid derivatives via a diastereoselective aldol/β-elimination sequence: Application to the C(15)-C(21) fragment of tedanolide C

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID; IMIDE; KETONE; MACROLIDE; TEDANOLIDE C;

EID: 77952344273     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1006955     Document Type: Article
Times cited : (12)

References (30)
  • 6
    • 77952407547 scopus 로고
    • Ger. Pat. 2,155,113. For reviews of the Baylis-Hillman reacdtion, see
    • Baylis, A. B.; Hillman, M. E. D. Ger. Pat. 2,155,113, 1972. For reviews of the Baylis-Hillman reacdtion, see
    • (1972)
    • Baylis, A.B.1    Hillman, M.E.D.2
  • 11
    • 77952328433 scopus 로고    scopus 로고
    • For reports of enantioselective Baylis-Hillman reactions with chiral acylate derivatives
    • For reports of enantioselective Baylis-Hillman reactions with chiral acylate derivatives
  • 14
    • 77952385891 scopus 로고    scopus 로고
    • note
    • For previous syntheses of racemic Baylis-Hillman adducts from aldol reactions of β-selenophenyl enolboranes see
  • 24
    • 77952388703 scopus 로고    scopus 로고
    • note
    • 4 gave a mixture of the 1,2- and the 1,4-reduced products in a 1:1 ratio.
  • 29
    • 77952328918 scopus 로고    scopus 로고
    • note
    • The stereochemistry of the C(16) hydroxy group was assigned based on the usual sense of asymmetric induction in Sharpless asymmetric dihydroxylation reactions, and was not rigorously determined at this stage.
  • 30
    • 77952346243 scopus 로고    scopus 로고
    • note
    • The two diastereomers were inseparable by standard column chromatography. Purification of the major diastereomer was performed by HPLC.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.