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Volumn 79, Issue 2, 2014, Pages 473-486

Total synthesis, stereochemical assignment, and biological activity of all known (-)-trigonoliimines

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOIDS; BIOACTIVITY; ENANTIOSELECTIVITY; METABOLITES; NITROGEN COMPOUNDS;

EID: 84896802062     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo4020358     Document Type: Article
Times cited : (71)

References (93)
  • 2
    • 33751335837 scopus 로고    scopus 로고
    • For a review on indolocarbazole natural products
    • For a review on indolocarbazole natural products, see: Sanchez, C.; Mendez, C.; Salas, J. A Nat. Prod. Rep. 2006, 23, 1007-1045.
    • (2006) Nat. Prod. Rep. , vol.23 , pp. 1007-1045
    • Sanchez, C.1    Mendez, C.2    Salas, J.3
  • 18
    • 84884835297 scopus 로고    scopus 로고
    • For another recent total synthesis of (±)-trigonoliimine C See
    • For another recent total synthesis of (±)-trigonoliimine C, see: Reddy, B. N.; Ramana, C. V Chem. Commun. 2013, 49, 9767-9769.
    • (2013) Chem. Commun. , vol.49 , pp. 9767-9769
    • Reddy, B.N.1    Ramana, C.V.2
  • 19
    • 84896781470 scopus 로고    scopus 로고
    • For elegant examples of the application of oxidation and rearrangement of 2,3-disubstituted indoles in complex syn thesis, see:
    • For elegant examples of the application of oxidation and rearrangement of 2,3-disubstituted indoles in complex synthesis, see:
  • 29
    • 0037326264 scopus 로고    scopus 로고
    • and references cited therein
    • Williams, R. M.; Cox, R. J. Acc. Chem. Res. 2003, 36, 127-139 and references cited therein.
    • (2003) Acc. Chem. Res. , vol.36 , pp. 127-139
    • Williams, R.M.1    Cox, R.J.2
  • 35
    • 84896756000 scopus 로고    scopus 로고
    • See the Supporting Information for details
    • See the Supporting Information for details.
  • 43
    • 35948974651 scopus 로고    scopus 로고
    • For an asymmetric oxidation of 2,3-disubstituted indole using chiral auxiliary
    • For an asymmetric oxidation of 2,3-disubstituted indole using chiral auxiliary, see: Pettersson, M.; Knueppel, D.; Martin, S. F. Org. Lett. 2007, 9, 4623-4626.
    • (2007) Org. Lett. , vol.9 , pp. 4623-4626
    • Pettersson, M.1    Knueppel, D.2    Martin, S.3
  • 44
    • 84862908013 scopus 로고    scopus 로고
    • For biosynthetic studies of asymmetric oxidation of the 2,3-disubstituted indole moiety of prenylated indole natural products and references therein
    • For biosynthetic studies of asymmetric oxidation of the 2,3-disubstituted indole moiety of prenylated indole natural products, see: Li, S.; Finefield, J. M.; Sunderhaus, J. D.; McAfoos, T. J.; Williams, R. M.; Sherman, D. H. J. Am. Chem. Soc. 2012, 134, 788-791 and references therein.
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 788-791
    • Li, S.1    Finefield, J.2    Sunderhaus, J.3    McAfoos, T.4    Williams, R.5    Sherman, D.6
  • 46
    • 84872175088 scopus 로고    scopus 로고
    • For An Application Of Aspartyl-based Asymmetric Oxidation In Total Synthesis
    • For an application of aspartyl-based asymmetric oxidation in total synthesis, see: Sun, M.; Hao, X.-Y.; Liu, S.; Hao, X.-J. Tetrahedron Lett. 2013, 54, 692-694.
    • (2013) Tetrahedron Lett. , Issue.54 , pp. 692-694
    • Sun, M.1    Hao, X.-Y.2    Liu, S.3    Hao, X.-J.4
  • 49
    • 84896783131 scopus 로고    scopus 로고
    • We finished the synthesis of the (±) 19-desmethoxytrigonoliimine C (33) on June 2010 and focused on the enantioselective total synthesis of all trigonoliimines since then
    • We finished the synthesis of the (±)-19-desmethoxytrigonoliimine C (33) on June 2010 and focused on the enantioselective total synthesis of all trigonoliimines since then.
  • 52
    • 84896803056 scopus 로고    scopus 로고
    • Treatment of hydroxyaminal 23 wih 3 equiv of Sc(OTf)3 in acetonitrile-toluene (2:1) at 81 °C provided a mixture of indoxyl and oxindole intermediates in good yield (indoxyl/oxindole = 4:1, >99%). However, nontrivial separation of these intermediates allowed only 31% isolated yield of a pure indoxyl intermediate
    • Treatment of hydroxyaminal 23 wih 3 equiv of Sc(OTf)3 in acetonitrile-toluene (2:1) at 81 °C provided a mixture of indoxyl and oxindole intermediates in good yield (indoxyl/oxindole = 4:1, >99%). However, nontrivial separation of these intermediates allowed only 31% isolated yield of a pure indoxyl intermediate.
  • 54
    • 0001688482 scopus 로고
    • For examples of C2-C2′ bond formation of two indoles using Stille cross-coupling reaction, see: (a)
    • For examples of C2-C2′ bond formation of two indoles using Stille cross-coupling reaction, see: (a) Palmisano, G.; Santagostino, M. Helv. Chim. Acta 1993, 76, 2356-2366.
    • (1993) Helv. Chim. Acta , Issue.76 , pp. 2356-2366
    • Palmisano, G.1    Santagostino, M.2
  • 60
    • 0030665853 scopus 로고    scopus 로고
    • For examples of C2-C2′ bond formation of two indoles using Suzuki-Miyaura cross-coupling reaction
    • For examples of C2-C2′ bond formation of two indoles using Suzuki-Miyaura cross-coupling reaction, see: (a) Merlic, C. A.; McInnes, D. M. Tetrahedron Lett. 1997, 38, 7661-7664.
    • (1997) Tetrahedron Lett. , Issue.38 , pp. 7661-7664
    • Merlic, C.1    McInnes, D.2
  • 78
    • 84896786519 scopus 로고    scopus 로고
    • An alternative reaction mechanism for the formation of (-)-trigonoliimine A (1) involves the initial imidate formation at N12 of (-)-12 followed by condensation intramolecular condensation with N13
    • An alternative reaction mechanism for the formation of(-)-trigonoliimine A (1) involves the initial imidate formation at N12 of (-)-12 followed by condensation intramolecular condensation with N13.
  • 80
    • 84896741839 scopus 로고    scopus 로고
    • For an excellent discussion of a similar scrambling of regioisomers during the 1,2-alkyl shift of a hydroxyindolenine, see ref 9
    • For an excellent discussion of a similar scrambling of regioisomers during the 1,2-alkyl shift of a hydroxyindolenine, see ref 9.
  • 82
    • 84896803845 scopus 로고    scopus 로고
    • Spartan ′06 was used for the calculations. For an X-ray crystal structure of (-)-trigonoliimine C (3), see ref 8
    • Spartan ′06 was used for the calculations. For an X-ray crystal structure of (-)-trigonoliimine C (3), see ref 8.
  • 83
    • 84896787378 scopus 로고    scopus 로고
    • For a report of similar air oxidation of a 2,2′-bistryptamine derivative, see ref 9
    • For a report of similar air oxidation of a 2,2′-bistryptamine derivative, see ref 9.
  • 90
    • 84896783922 scopus 로고    scopus 로고
    • Acetic acid-d4 (1.1 equiv) was added, resulting in sharpening of peaks
    • Acetic acid-d4 (1.1 equiv) was added, resulting in sharpening of peaks.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.