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Volumn 4, Issue 17, 2002, Pages 2977-2980

Highly stereoselective and stereodivergent synthesis of four types of THF cores in acetogenins using a C4-chiral building block

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKYNE; ANTINEOPLASTIC AGENT; FURAN DERIVATIVE;

EID: 0001320812     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026393j     Document Type: Article
Times cited : (49)

References (34)
  • 25
    • 84872274587 scopus 로고    scopus 로고
    • note
    • From a model study using chiral lactaldehyde TBS ether and the alkyne (S)-4, we found that a combination of the (R)-aldehyde and (S)-4 provided better yield and selectivity than that of (S)-aldehyde and (S)-4.
  • 27
    • 84872272643 scopus 로고    scopus 로고
    • note
    • The diastereomeric ratio based on the benzylidene acetal for 8a and 8b was almost same as the ratio of 7a and 7b used.
  • 30
    • 84872263490 scopus 로고    scopus 로고
    • note
    • 1H NMR spectral data of the syn adducts 8a appeared upfield by 0.1-0.2 ppm from those in the anti adducts 8b. On the other hand, the signals of the OH proton in the syn adducts appeared downfield by 0.1-0.2 ppm from that in the anti adducts. The shifts were consistent for each compound in this series.
  • 33
    • 84872263772 scopus 로고    scopus 로고
    • note
    • An attempt to obtain 10b via tosylation of 8a followed by simultaneous reduction of the triple bond and the benzylidene acetal failed presumably due to hydrogenolysis of the tosyl group.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.