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Volumn 9, Issue 25, 2007, Pages 5267-5270

Construction of epidithiodioxopiperazines by directed oxidation of hydroxyproline-derived dioxopiperazines

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL PRODUCT; ETHER; HYDROXYPROLINE; OXYGEN; PIPERAZINE DERIVATIVE; THIOL DERIVATIVE; TRYPTOPHAN;

EID: 37249068440     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702518t     Document Type: Article
Times cited : (47)

References (54)
  • 23
    • 0001272994 scopus 로고    scopus 로고
    • For synthetic studies toward cyclotryptophan-containing ETPs by other groups, see: a
    • For synthetic studies toward cyclotryptophan-containing ETPs by other groups, see: (a) Crich, D.; Fredette, E.; Flosi, W. J. Heterocycles 1998, 48, 545-547.
    • (1998) Heterocycles , vol.48 , pp. 545-547
    • Crich, D.1    Fredette, E.2    Flosi, W.J.3
  • 25
    • 33846599334 scopus 로고    scopus 로고
    • For the recent total synthesis of a related, structurally simpler cyclotryptophan alkaloid, see
    • For the recent total synthesis of a related, structurally simpler cyclotryptophan alkaloid, see: Overman, L. E.; Shin, Y. Org. Lett. 2007, 9, 339-341.
    • (2007) Org. Lett , vol.9 , pp. 339-341
    • Overman, L.E.1    Shin, Y.2
  • 26
    • 0001279669 scopus 로고
    • For an early example of 1,5-radical translocation from a protecting group, see
    • For an early example of 1,5-radical translocation from a protecting group, see: Curran, D. P.; Kim, D.; Liu, H. T.; Shen, W. J. Am. Chem. Soc. 1988, 110, 5900-5902.
    • (1988) J. Am. Chem. Soc , vol.110 , pp. 5900-5902
    • Curran, D.P.1    Kim, D.2    Liu, H.T.3    Shen, W.4
  • 27
    • 0000476739 scopus 로고    scopus 로고
    • For examples of C-H bond oxidation α to oxygen of alcohol derivatives, see: (a) Lewin, A. H, Dinwoodie, A. H, Cohen, T. Tetrahedron 1966, 22, 1527-1537
    • For examples of C-H bond oxidation α to oxygen of alcohol derivatives, see: (a) Lewin, A. H.; Dinwoodie, A. H.; Cohen, T. Tetrahedron 1966, 22, 1527-1537.
  • 30
    • 0001179642 scopus 로고    scopus 로고
    • For examples of C-H bond oxidation δ to oxygen of alcohol derivatives, see: (a) Barton, D. H. R, Beaton, J. M, Geller, L. E, Pechet, M. M. J. Am. Chem. Soc. 1960, 82, 2640-2641
    • For examples of C-H bond oxidation δ to oxygen of alcohol derivatives, see: (a) Barton, D. H. R.; Beaton, J. M.; Geller, L. E.; Pechet, M. M. J. Am. Chem. Soc. 1960, 82, 2640-2641.
  • 31
    • 0029036335 scopus 로고
    • For recent reviews, see: b
    • For recent reviews, see: (b) Majetich, G.; Wheless, K. Tetrahedron 1995, 51, 7095-7129.
    • (1995) Tetrahedron , vol.51 , pp. 7095-7129
    • Majetich, G.1    Wheless, K.2
  • 32
    • 0035372638 scopus 로고    scopus 로고
    • (c) Reese, P. B. Steroids 2001, 66, 481-497.
    • (2001) Steroids , vol.66 , pp. 481-497
    • Reese, P.B.1
  • 35
    • 0028122946 scopus 로고
    • Intramolecular hydrogen atom abstraction β to a protected alcohol, followed by C-C bond formation or trapping with hydrogen has been described; see: a
    • Intramolecular hydrogen atom abstraction β to a protected alcohol, followed by C-C bond formation or trapping with hydrogen has been described; see: (a) Brunckova, J.; Crich, D.; Yao, Q. Tetrahedron Lett. 1994, 35, 6619-6622.
    • (1994) Tetrahedron Lett , vol.35 , pp. 6619-6622
    • Brunckova, J.1    Crich, D.2    Yao, Q.3
  • 41
    • 37249040724 scopus 로고    scopus 로고
    • Synthesis of 3-hydroxyproline derivative 6 is described in the Supporting Information.
    • Synthesis of 3-hydroxyproline derivative 6 is described in the Supporting Information.
  • 43
    • 37249092736 scopus 로고    scopus 로고
    • Attempted cleavage of the TBS group under several other conditions (TBAF, HF/pyridine, or MeOH in HCl) led to significant decomposition
    • Attempted cleavage of the TBS group under several other conditions (TBAF, HF/pyridine, or MeOH in HCl) led to significant decomposition.
  • 44
    • 0000079538 scopus 로고
    • For pioneering studies of the use of (bromomethyl)dimethylsiloxy ethers in free radical chain reactions, see: a
    • For pioneering studies of the use of (bromomethyl)dimethylsiloxy ethers in free radical chain reactions, see: (a) Nishiyama, H.; Kitajima, T.; Matsumoto, M.; Itoh, K. J. Org. Chem. 1984, 49, 2298-2300.
    • (1984) J. Org. Chem , vol.49 , pp. 2298-2300
    • Nishiyama, H.1    Kitajima, T.2    Matsumoto, M.3    Itoh, K.4
  • 46
    • 37249000089 scopus 로고    scopus 로고
    • The synthesis of α-bromomethylsilyl 13 is described in the Supporting Information.
    • The synthesis of α-bromomethylsilyl 13 is described in the Supporting Information.
  • 47
    • 37249092236 scopus 로고    scopus 로고
    • In an early calibration experiment, the reaction of iodoacetal i with tributyltin hydride, AIBN, and TEMPO in benzene at 85°C resulted only in substitution at the acetal substituent to provide TEMPO adduct ii. This result showed that the primary radical derived from i was trapped with TEMPO faster than it underwent 1,5-hydrogen atom transfer
    • In an early calibration experiment, the reaction of iodoacetal i with tributyltin hydride, AIBN, and TEMPO in benzene at 85°C resulted only in substitution at the acetal substituent to provide TEMPO adduct ii. This result showed that the primary radical derived from i was trapped with TEMPO faster than it underwent 1,5-hydrogen atom transfer.
  • 48
    • 37249068715 scopus 로고    scopus 로고
    • These modifications were developed during contemporaneous studies of the oxidation of an analogue of 12 having an isopropylidene substituent at C3
    • These modifications were developed during contemporaneous studies of the oxidation of an analogue of 12 having an isopropylidene substituent at C3.
  • 49
    • 37249086403 scopus 로고    scopus 로고
    • The relative configuration of these products was determined by NOESY NMR experiments; see the Supporting Information for details
    • The relative configuration of these products was determined by NOESY NMR experiments; see the Supporting Information for details.
  • 50
    • 37249070552 scopus 로고    scopus 로고
    • 2 could be reduced to 7 equiv; however, yields of angular oxidation were maximized by using an equal excess of the silane.
    • 2 could be reduced to 7 equiv; however, yields of angular oxidation were maximized by using an equal excess of the silane.
  • 51
    • 37249085327 scopus 로고    scopus 로고
    • The construction of epidithiodioxopiperazines from dioxopiperazines that contain two leaving groups by ZnCl2-promoted reaction of H 2S has been reported; see refs 4d, 4e, 4k, and 41
    • 2S has been reported; see refs 4d, 4e, 4k, and 41.
  • 52
    • 37249002054 scopus 로고    scopus 로고
    • More conventional conditions for removing the acetate group were not compatible with the disulfide bridge
    • More conventional conditions for removing the acetate group were not compatible with the disulfide bridge.
  • 53
    • 37249011563 scopus 로고    scopus 로고
    • CCDC 663428. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
    • CCDC 663428. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.