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Volumn 62, Issue 22, 2006, Pages 5318-5337

Synthetic ventures inspired by biosynthetic hypotheses: the evolution of a method for the oxidative amidation of phenols

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID DERIVATIVE; CYLINDRICINE C; FR 901483; IMMUNOSUPPRESSIVE AGENT; NATURAL PRODUCT; PHENOL DERIVATIVE; TAN 1251C; UNCLASSIFIED DRUG;

EID: 33646493497     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.01.111     Document Type: Article
Times cited : (60)

References (181)
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    • note
    • This course was given at the University of Michigan by the senior author's doctoral advisor, Prof. Masato Koreeda, to whom we are pleased to dedicate this article.
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    • See also:
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    • note
    • 50≈510 nM; tests conducted at the U.S. NCI).
  • 15
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    • Review:
  • 17
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    • Isolation:
  • 19
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    • Enantiocontrolled total syntheses:
  • 22
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    • Syntheses of the racemate:
  • 25
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    • Synthetic studies:
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    • Kropf, J. E.; Weinreb, S. M. Abstracts of Papers, 222nd National Meeting of the American Chemical Society, Chicago, IL, Aug 26-30, 2001; American Chemical Society: Washington, DC, 2001; ORGN 373;
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    • Shirafuji, H.; Tsubotani, S.; Ishimaru, T.; Harada, S. (Takeda Chemical Industries, Ltd.) WO91/13887, 1991
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    • Implicit in the formulation of Scheme 4 is the notion that 21 will advance to spirolactam 20 through oxidative conversion of the phenol to an electrophilic species, perhaps a cationic agent of the type 27 (cf. Scheme 6), which is then captured by the nitrogen atom of the amide. The N atom thus expresses nucleophilic character in this transformation. Complementary reactions also leading to spirolactams, but involving reaction of an electron-rich aromatic ring with an electrophilic N atom, were known prior to our work. Notable in this regard is the chemistry of N-alkoxy-acylnitrenium species (cf.
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    • ), which in recent years has revealed its full synthetic potential thanks to the work of Wardrop
    • Kikugawa Y., Shimada M., and Matsumoto K. Heterocycles 37 (1994) 293 ), which in recent years has revealed its full synthetic potential thanks to the work of Wardrop
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    • Kikugawa, Y.1    Shimada, M.2    Matsumoto, K.3
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    • For leading references see:
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    • See also:
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    • Oxazolines also participate effectively in iodolactamization reactions:
    • Oxazolines also participate effectively in iodolactamization reactions:. Kurth M.J., and Bloom S.H. J. Org. Chem. 54 (1989) 411
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    • Kurth, M.J.1    Bloom, S.H.2
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    • For example the Wipf method: reference
  • 64
    • 0000892411 scopus 로고    scopus 로고
    • This entails conduct of the reaction in fluorinated alcohol solvents such as hexafluoro-2-propanol (HFIP) or trifluoroethanol (TFE). Cf. Ref. 12 as well as:
    • This entails conduct of the reaction in fluorinated alcohol solvents such as hexafluoro-2-propanol (HFIP) or trifluoroethanol (TFE). Cf. Ref. 12 as well as:. Kita Y., Takada T., Gyoten M., Tohma H., Zenk M.H., and Eichhorn J. J. Org. Chem. 61 (1996) 5857
    • (1996) J. Org. Chem. , vol.61 , pp. 5857
    • Kita, Y.1    Takada, T.2    Gyoten, M.3    Tohma, H.4    Zenk, M.H.5    Eichhorn, J.6
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    • 33646472697 scopus 로고    scopus 로고
    • Cf.:
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    • See also:
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    • For additional applications of this transformation, which one may rightfully describe as the Sorensen reaction, see, e.g.:
    • For additional applications of this transformation, which one may rightfully describe as the Sorensen reaction, see, e.g.:. Mizutani H., Takayama J., Soeda Y., and Honda T. Tetrahedron Lett. 43 (2002) 2411
    • (2002) Tetrahedron Lett. , vol.43 , pp. 2411
    • Mizutani, H.1    Takayama, J.2    Soeda, Y.3    Honda, T.4
  • 71
    • 33646485747 scopus 로고    scopus 로고
    • Synthesis of TAN1251 substances:
  • 78
    • 33646472377 scopus 로고    scopus 로고
    • Synthetic studies:
  • 90
    • 33646466742 scopus 로고    scopus 로고
    • For example:
  • 97
    • 33646489733 scopus 로고    scopus 로고
    • note
    • The lactam unit in 57 is much less C-H acidic than either the ketone or the aldehyde, and it was anticipated not to interfere with the operations leading to the tricyclic aldol intermediate.
  • 99
    • 33646491111 scopus 로고    scopus 로고
    • note
    • Dielectric constants at 25 °C (CRC Handbook of Chemistry and Physics, 59th Ed.): t-BuOH=10.9; EtOH=24.3; MeOH=32.6.
  • 100
    • 33646487100 scopus 로고    scopus 로고
    • note
    • The OH group is more accessible in the less sterically hindered MeOH and EtOH relative to the more sterically encumbered t-BuOH. This should result in stronger H-bonds.
  • 102
    • 33646483612 scopus 로고    scopus 로고
    • note
    • We are grateful to the Fujisawa Co. for a sample of nature FR-901483.
  • 106
    • 33646486967 scopus 로고    scopus 로고
    • note
    • The absolute configuration of natural cylindricines remains unknown. We focused on (-)-cylindricine C, 76, only because we intended to compare our ultimate product with that described by Molander (Ref. 35a), who at the onset of our investigations was the sole author to have achieved the enantiocontrolled synthesis of a cylindricine.
  • 107
    • 33646485061 scopus 로고    scopus 로고
    • Enantiocontrolled syntheses of various cylindricines:
  • 109
    • 33646474533 scopus 로고    scopus 로고
    • C, D, and E:
  • 114
    • 33646475074 scopus 로고    scopus 로고
    • Syntheses of (±)-cylindricines:
  • 117
    • 33646474948 scopus 로고    scopus 로고
    • (±)-4-Epicylindricine C:
  • 119
    • 33646493277 scopus 로고    scopus 로고
    • Synthetic studies:
  • 124
    • 33646483882 scopus 로고    scopus 로고
    • Studies on structurally related alkaloids:
  • 136
    • 33646494129 scopus 로고    scopus 로고
    • note
    • The unnatural aminoacid, homotyrosine, is commercially available in either enantiomeric form
  • 141
    • 33646491381 scopus 로고    scopus 로고
    • note
    • In principle, all cylindricines may be obtained by appropriate manipulations of cylindricine C, which therefore is a privileged target for chemical synthesis.
  • 142
    • 0042530467 scopus 로고    scopus 로고
    • Other protecting groups afforded inferior diastereoselectivities. For the use of bulky silyl groups to direct facial selectivity in a different context see, e.g.:
    • Other protecting groups afforded inferior diastereoselectivities. For the use of bulky silyl groups to direct facial selectivity in a different context see, e.g.:. Clive D.L.J., and Wang J. Angew. Chem., Int. Ed. 42 (2003) 3406
    • (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 3406
    • Clive, D.L.J.1    Wang, J.2
  • 144
    • 33646489734 scopus 로고    scopus 로고
    • For a discussion see:
  • 146
    • 33646493278 scopus 로고    scopus 로고
    • See also
  • 151
    • 33646486499 scopus 로고    scopus 로고
    • See also:
  • 155
    • 33646493602 scopus 로고    scopus 로고
    • note
    • ® (registered trademark of the DuPont Co.). Presumably, this Bronsted acidic reagent rapidly protonated the tertiary amino group in 107, thereby suppressing possible interference during oxidation of the thioether.
  • 158
    • 33646486344 scopus 로고    scopus 로고
    • For amine-directed organocuprate additions see, e.g.:
  • 160
    • 33646466741 scopus 로고    scopus 로고
    • Bibliography on directed organocuprate additions:
  • 164
    • 33646492732 scopus 로고    scopus 로고
    • note
    • By contrast, the Wardrop cyclization of N-alkoxy-acylnitrenium ions (Refs. 11g-j) leading to N-alkoxy piperidinones occurs efficiently.
  • 165
    • 33646476948 scopus 로고    scopus 로고
    • note
    • These experiments were inspired by the success of our sulfonamide-based methodology (Ref. 3).
  • 166
    • 33646485197 scopus 로고    scopus 로고
    • Leading references and noteworthy examples of reactions of this type: see Refs. 11 as well as:


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.