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Volumn 47, Issue 47, 2006, Pages 8413-8417

Synthesis towards complex bridged alkaloids derived from diketopiperazines: a cationic cascade approach to stephacidins, paraherquamides and related systems

Author keywords

Cationic cyclisation; Diketopiperazine; Paraherquamide; Stephacidin

Indexed keywords

ALKALOID DERIVATIVE; BICYCLO[2.2.2]OCTANE DERIVATIVE; PARAHERQUAMIDE DERIVATIVE; PIPERAZINEDIONE; STEPHACIDIN; UNCLASSIFIED DRUG;

EID: 33750007357     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.09.046     Document Type: Article
Times cited : (4)

References (39)
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    • For another synthesis of stephacidin B, see:
    • For another synthesis of stephacidin B, see:. Herzon S.B., and Myers A.G. J. Am. Chem. Soc. 127 (2005) 5342
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 5342
    • Herzon, S.B.1    Myers, A.G.2
  • 23
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    • For enolisation-substitution of cyclo(Pro, Pro), see:
    • For enolisation-substitution of cyclo(Pro, Pro), see:. Poullennec K.G., Kelly A.T., and Romo D. Org. Lett. 4 (2002) 2645
    • (2002) Org. Lett. , vol.4 , pp. 2645
    • Poullennec, K.G.1    Kelly, A.T.2    Romo, D.3
  • 25
    • 33947302252 scopus 로고
    • Our DKP synthesis follows along known lines, see for example:
    • Our DKP synthesis follows along known lines, see for example:. Nitecki D.E., Halpern B., and Wesley J.W. J. Org. Chem. 33 (1968) 864
    • (1968) J. Org. Chem. , vol.33 , pp. 864
    • Nitecki, D.E.1    Halpern, B.2    Wesley, J.W.3
  • 28
    • 33749985681 scopus 로고    scopus 로고
    • note
    • + 433.2486. We observed that effective substitution required ca.1.5 equiv of base for 9a; ca. 2 equiv for 9b; and ca. 3 equiv for 9c.
  • 29
    • 33750033196 scopus 로고    scopus 로고
    • note
    • The diastereomeric mixtures obtained for 19a (1:1), 19b (2:1) and 19c (3.3:1) seem to reflect poor control in a looser transition state than the other reactions-presumably a result of a relatively long C-S bond, although we have not ruled out epimerisation as yet. Benzaldehyde aldols 20a and 20b are single diastereomers, but we have not yet unequivocally assigned the configuration at the new carbinol centre in these adducts.
  • 30
    • 33750021387 scopus 로고    scopus 로고
    • note
    • The figure shows one of the two crystallographically independent molecules. Displacement ellipsoids are drawn at 30% probability level. The structure has been deposited at the Cambridge Crystallographic Data Centre, deposition number CCDC 617970.
  • 31
    • 33749984182 scopus 로고    scopus 로고
    • note
    • The reasons for the effectiveness of base 21 are not clear at this time.
  • 32
    • 33749989025 scopus 로고    scopus 로고
    • note
    • +, 10%). A sample for X-ray crystal structure determination was prepared from DKP 22 (25 mg) via vapour diffusion from EtOAc (0.5 mL) and petrol (5 mL) over a period of seven days.
  • 34
    • 0010036491 scopus 로고    scopus 로고
    • For a relevant review, see:
    • For a relevant review, see:. Liebscher J., and Jin S. Chem. Soc. Rev. 28 (1999) 251
    • (1999) Chem. Soc. Rev. , vol.28 , pp. 251
    • Liebscher, J.1    Jin, S.2
  • 37
    • 33750023401 scopus 로고    scopus 로고
    • note
    • + 431.2302.
  • 38
    • 9944263397 scopus 로고    scopus 로고
    • This procedure was based on related N-acyliminium chemistry of DKPs, reported by Davies and co-workers, see for example:
    • This procedure was based on related N-acyliminium chemistry of DKPs, reported by Davies and co-workers, see for example:. Bull S.D., Davies S.G., Garner A.C., Savory E.D., Snow E.J., and Smith A.D. Tetrahedron: Asymmetry 15 (2004) 3989
    • (2004) Tetrahedron: Asymmetry , vol.15 , pp. 3989
    • Bull, S.D.1    Davies, S.G.2    Garner, A.C.3    Savory, E.D.4    Snow, E.J.5    Smith, A.D.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.