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Volumn 41, Issue 24, 2002, Pages 4686-4688

Facile construction of N-hydroxybenzazocine: Enantioselective total synthesis of (+)-FR900482

Author keywords

Aldol reaction; Antitumor agents; Asymmetric synthesis; Hydroxylamines; Natural products; Total synthesis

Indexed keywords

ANTIBIOTICS; HYDROGEN BONDS; MOLECULAR STRUCTURE; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL); TUMORS;

EID: 0037122102     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200290016     Document Type: Article
Times cited : (60)

References (34)
  • 19
    • 0001198102 scopus 로고    scopus 로고
    • After submission of this manuscript, we learned that two groups have independently completed enantioselective total syntheses; see the previous communication: a) T. C. Jude, R. M. Williams, Angew. Chem. 2002, 114, 4877; Angew. Chem. Int. Ed. 2002, 41, 4683; and the following communication: b) R. Ducray, M. A. Ciufolini, Angew. Chem. 2002, 114, 4882; Angew. Chem. Int. Ed. 2002, 41, 4688.
    • (2002) Angew. Chem. , vol.114 , pp. 4877
    • Jude, T.C.1    Williams, R.M.2
  • 20
    • 0037122113 scopus 로고    scopus 로고
    • After submission of this manuscript, we learned that two groups have independently completed enantioselective total syntheses; see the previous communication: a) T. C. Jude, R. M. Williams, Angew. Chem. 2002, 114, 4877; Angew. Chem. Int. Ed. 2002, 41, 4683; and the following communication: b) R. Ducray, M. A. Ciufolini, Angew. Chem. 2002, 114, 4882; Angew. Chem. Int. Ed. 2002, 41, 4688.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 4683
  • 21
    • 0001210837 scopus 로고    scopus 로고
    • After submission of this manuscript, we learned that two groups have independently completed enantioselective total syntheses; see the previous communication: a) T. C. Jude, R. M. Williams, Angew. Chem. 2002, 114, 4877; Angew. Chem. Int. Ed. 2002, 41, 4683; and the following communication: b) R. Ducray, M. A. Ciufolini, Angew. Chem. 2002, 114, 4882; Angew. Chem. Int. Ed. 2002, 41, 4688.
    • (2002) Angew. Chem. , vol.114 , pp. 4882
    • Ducray, R.1    Ciufolini, M.A.2
  • 22
    • 0037121441 scopus 로고    scopus 로고
    • After submission of this manuscript, we learned that two groups have independently completed enantioselective total syntheses; see the previous communication: a) T. C. Jude, R. M. Williams, Angew. Chem. 2002, 114, 4877; Angew. Chem. Int. Ed. 2002, 41, 4683; and the following communication: b) R. Ducray, M. A. Ciufolini, Angew. Chem. 2002, 114, 4882; Angew. Chem. Int. Ed. 2002, 41, 4688.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 4688
  • 27
    • 0346854824 scopus 로고    scopus 로고
    • note
    • 3N) gave a considerable amount of the homocoupling by-product of the acetylene.
  • 30
    • 0347485325 scopus 로고    scopus 로고
    • note
    • 1H NMR spectroscopy. The structure of 21 was unambiguously confirmed by observation of NOE interactions between 7-H and 9-H.
  • 31
    • 0348115496 scopus 로고    scopus 로고
    • note
    • In addition to 22, formation of a side product, which was tentatively assigned as hydroxylamine hemiacetal diastereomer 22′, was observed. This mixture was subjected to the next acetonide formation without separation.
  • 32
    • 0346854825 scopus 로고    scopus 로고
    • note
    • The ratio of 22/22′ was almost the same as that of 23 and a side product, which was tentatively assigned as 23′. Furthermore, deprotection of the acetonide of 23 and 23′ under acidic conditions (HCl (1N) in THF, room temperature) gave only 22 and 22′, respectively. These observations would indicate that neither epimerization of C7 nor interconversion of the hemiacetal diastereomers via the eight-membered ring ketone occurred during the acetonide formation.
  • 34
    • 0346854823 scopus 로고    scopus 로고
    • note
    • The aldehyde was protected as the dimethyl acetal to prevent reduction during hydrogenolysis of the phenolic benzyl ether.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.