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Volumn 3, Issue 10, 2001, Pages 1551-1554

Synthesis and Determination of Absolute Configuration of the Bicyclic Guanidine Core of Batzelladine A

Author keywords

[No Author keywords available]

Indexed keywords

4 (SULFONO(DIFLUOROMETHYL)PHENYLALANINE); 4-(SULFONO(DIFLUOROMETHYL)PHENYLALANINE); ALKALOID; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; DRUG DERIVATIVE; GUANIDINE DERIVATIVE; PHENYLALANINE;

EID: 0035902249     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015848m     Document Type: Article
Times cited : (36)

References (27)
  • 17
    • 0026535626 scopus 로고
    • The bicyclic guanidine portion of 1 is virtually identical to crambescin/ crambine A, which has an 11-carbon saturated alkyl side chain. For a biomimetic synthesis of racemic crambescins/crambines, see: (a) Snider, B. B.; Shi, Z. J. Org. Chem. 1992, 57, 2526-2528.
    • (1992) J. Org. Chem. , vol.57 , pp. 2526-2528
    • Snider, B.B.1    Shi, Z.2
  • 19
    • 0041705558 scopus 로고    scopus 로고
    • note
    • Carbon number labeling is in accordance with the original isolation paper (ref 1a).
  • 21
    • 0027744195 scopus 로고
    • α-Bromination to form 7 proceeded via a modification of the reported procedure (Hanessian, S.; Vanasse, B.; Yang, H.; Alpegiani, M. Can. J. Chem. 1993, 71, 1407-1411) in order to minimize unwanted α-dibromination (see Supporting Information).
    • (1993) Can. J. Chem. , vol.71 , pp. 1407-1411
    • Hanessian, S.1    Vanasse, B.2    Yang, H.3    Alpegiani, M.4
  • 24
    • 0043208321 scopus 로고    scopus 로고
    • note
    • It is likely that treatment of 9E/Z with 2.2 equiv of NaH led to formation of the E-dianion, which underwent efficient cyclic urea formation.
  • 25
    • 0041705556 scopus 로고    scopus 로고
    • note
    • The use of 5 equiv of NaH for urea formation led to an increase in the isolated yield of the urea 10, although partial racemization led to the formation of a 3:1 mixture of enantiomers as evidenced by Mosher ester analysis of intermediate of 15. The use of 2.2 equiv of NaH minimized the extent of racemization to form 10 (er, 95:05).
  • 26
    • 0041705557 scopus 로고    scopus 로고
    • note
    • The use of 2,4,6-tri(tert-butyl)pyridine as an acid scavenger led to N-methylation.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.