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Volumn 9, Issue 17, 2007, Pages 3331-3334

One-step synthesis of heteroaromatic-fused pyrrolidines via cyclopropane ring-opening reaction: Application to the PKCβ inhibitor JTT-010

Author keywords

[No Author keywords available]

Indexed keywords

(2R) 3 (2 AMINOMETHYL 2,3 DIHYDRO 1H 3A AZACYCLOPENTA(A)INDEN 8 YL) 4 PHENYLAMINOPYRROLE 2,5 DIONE MONOMETHANESULPHONATE; (2R)-3-(2-AMINOMETHYL-2,3-DIHYDRO-1H-3A-AZACYCLOPENTA(A)INDEN-8-YL)-4-PHENYLAMINOPYRROLE-2,5-DIONE MONOMETHANESULPHONATE; CYCLOPROPANE; CYCLOPROPANE DERIVATIVE; ENZYME INHIBITOR; HETEROCYCLIC COMPOUND; INDAN DERIVATIVE; PROTEIN KINASE C; PROTEIN KINASE C BETA; PYRROLE DERIVATIVE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 34548157997     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol071336h     Document Type: Article
Times cited : (87)

References (49)
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    • Homo [3 + 2] dipolar cycloaddition: (a) Young, I. S.; Williams, J. L.; Kerr, M. A. Org. Lett. 2005, 7, 953-955.
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    • The asymmetric Rh-catalyzed 1-allylindole C(2)-H bond activation has recently been applied successfully to the synthesis of a JTT-010 analogue. (a) For Rh-catalyzed C(2)-H bond activation of 1-allylindoles, see: Thalji, R. K.; Ellman, J. A.; Bergman, R. G. J. Am. Chem. Soc. 2004, 126, 7192-7193.
    • The asymmetric Rh-catalyzed 1-allylindole C(2)-H bond activation has recently been applied successfully to the synthesis of a JTT-010 analogue. (a) For Rh-catalyzed C(2)-H bond activation of 1-allylindoles, see: Thalji, R. K.; Ellman, J. A.; Bergman, R. G. J. Am. Chem. Soc. 2004, 126, 7192-7193.
  • 26
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    • Compound 2b was prepared from (R)-epichlorohydrin and diethyl malonate via one step. See: Sekiyama, T.; Hatsuya, S.; Tanaka, Y.; Uchiyama, M.; Ono, N.; Iwayama, S.; Oikawa, M.; Suzuki, K.; Okunishi, M.; Tsuji, T. J. Med. Chem. 1998, 41, 1284-1298.
    • Compound 2b was prepared from (R)-epichlorohydrin and diethyl malonate via one step. See: Sekiyama, T.; Hatsuya, S.; Tanaka, Y.; Uchiyama, M.; Ono, N.; Iwayama, S.; Oikawa, M.; Suzuki, K.; Okunishi, M.; Tsuji, T. J. Med. Chem. 1998, 41, 1284-1298.
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    • See Supporting Information for X-ray crystallographic data of 7. Oxidation of 7 followed by methyl esterification gave 9, defining the absolute configuration of 7 as depicted because 9 was also obtained from 8a, whose absolute configuration was authenticated by its conversion to JTT-010.
    • See Supporting Information for X-ray crystallographic data of 7. Oxidation of 7 followed by methyl esterification gave 9, defining the absolute configuration of 7 as depicted because 9 was also obtained from 8a, whose absolute configuration was authenticated by its conversion to JTT-010.
  • 31
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    • Another reaction pathway involving nucleophilic attack at the methylene of 2b followed by decarboxylation and cyclization was ruled out since this pathway should not provide 7 but the enantiomer of 7
    • Another reaction pathway involving nucleophilic attack at the methylene of 2b followed by decarboxylation and cyclization was ruled out since this pathway should not provide 7 but the enantiomer of 7.
  • 32
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    • Compound If was prepared in one step from 2-oxindole. See the Supporting Information.
    • Compound If was prepared in one step from 2-oxindole. See the Supporting Information.
  • 33
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    • Unpurified 2b was used in this 100 g scale reaction batch
    • Unpurified 2b was used in this 100 g scale reaction batch.
  • 34
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    • For decarboxylation of an indole-2-acetic acid derivative, see
    • (a) For decarboxylation of an indole-2-acetic acid derivative, see: Ho, B. T.; Walker, K. E. Org. Synth. 1988, VI, 965-966.
    • (1988) Org. Synth , vol.6 , pp. 965-966
    • Ho, B.T.1    Walker, K.E.2
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  • 36
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    • In this case, iterative operation was required to complete the reaction because partial lactone regeneration was competitive with the decarboxylation under acidic conditions
    • (c) In this case, iterative operation was required to complete the reaction because partial lactone regeneration was competitive with the decarboxylation under acidic conditions.
  • 37
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    • One of the minor isomers isolated from products of a chiral nitrone cycloaddition reaction was reportedly transformed into 10 ∼1% overall yield, Beccalli, E. M, Broggini, G, Rosa, C. L, Passarella, D, Pilati, T, Terraneo, A, Zecchi, G. J. Org. Chem. 2000, 65, 8924-8932
    • One of the minor isomers isolated from products of a chiral nitrone cycloaddition reaction was reportedly transformed into 10 (∼1% overall yield). Beccalli, E. M.; Broggini, G.; Rosa, C. L.; Passarella, D.; Pilati, T.; Terraneo, A.; Zecchi, G. J. Org. Chem. 2000, 65, 8924-8932.
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    • Degener, E.; Schmelzer, H. G.; Frohberger, P. F. Br. Patent 1145583, Mar 19, 1969.
    • (a) Degener, E.; Schmelzer, H. G.; Frohberger, P. F. Br. Patent 1145583, Mar 19, 1969.
  • 39
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    • Chem. Abstr. 1969, 70, 114648t.
    • (b) Chem. Abstr. 1969, 70, 114648t.
  • 42


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.