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Volumn 13, Issue 4, 2011, Pages 576-579

Highly regio-and stereoselective one-pot synthesis of carbohydrate-based butyrolactones

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; CARBOHYDRATE; DRUG DERIVATIVE; GAMMA BUTYROLACTONE; MAGNESIUM;

EID: 79951630485     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102723c     Document Type: Article
Times cited : (35)

References (28)
  • 24
    • 79951593833 scopus 로고    scopus 로고
    • Correlations between C-3 (δ 58.3)/H-7 (δ 2.67), H-3 (δ 4.18)/C-7 (δ 29.0), C-1 (δ 97.7)/H-7 (δ 2.67), and H-1 (δ 5.69)/C-7(δ 29.0) are in full agreement with the proposed structure. No correlation was observed between H-4 (δ 5.19) and the methylene carbon of lactone moiety, which ruled out the other regioisomer.
    • Correlations between C-3 (δ 58.3)/H-7 (δ 2.67), H-3 (δ 4.18)/C-7 (δ 29.0), C-1 (δ 97.7)/H-7 (δ 2.67), and H-1 (δ 5.69)/C-7(δ 29.0) are in full agreement with the proposed structure. No correlation was observed between H-4 (δ 5.19) and the methylene carbon of lactone moiety, which ruled out the other regioisomer.
  • 25
    • 79951664072 scopus 로고    scopus 로고
    • Correlations of H-1β/H-2, H-1β/H-3 in the NOESY experiments of 4a reveal that H-1, H-2, and H-3 are cofacial, which confirms the α-α ring juncture stereochemistry of bicyclic lactone.
    • Correlations of H-1β/H-2, H-1β/H-3 in the NOESY experiments of 4a reveal that H-1, H-2, and H-3 are cofacial, which confirms the α-α ring juncture stereochemistry of bicyclic lactone.
  • 28
    • 79951633173 scopus 로고    scopus 로고
    • The attack of the carboxy methylene radical bonded to the manganese, which may also coordinate with α-disposed anomeric substitutents, could be an alternative explanation for the exclusive α C-C bond formation leading to α-α lactonization as suggested by one of the reviewers.
    • The attack of the carboxy methylene radical bonded to the manganese, which may also coordinate with α-disposed anomeric substitutents, could be an alternative explanation for the exclusive α C-C bond formation leading to α-α lactonization as suggested by one of the reviewers.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.