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Volumn 132, Issue 20, 2010, Pages 7119-7137

Scalable total syntheses of N -linked tryptamine dimers by direct indole-aniline coupling: Psychotrimine and kapakahines B and F

Author keywords

[No Author keywords available]

Indexed keywords

DIASTEREOSELECTIVITIES; ELECTROPHILIC ATTACK; GRAM SCALE; N-LINKED; QUATERNIZATION; TOTAL SYNTHESIS; TRYPTAMINES;

EID: 77952559330     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja1009458     Document Type: Article
Times cited : (162)

References (165)
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    • The perturbation of pH in a restricted environment, such as an enzyme pocket, is well known; however, the necessity for strong base reduces the likelihood of such a transformation.
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    • See Figure 11 for excellent diastereoselectivities in the oxidative coupling reaction.
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    • The postulated difference between torsional strains of the transition states, as compared to that of the products, is suggested to arise from differing hybridization of the carbamate nitrogen lone pair. See ref 38b for further discussion.
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    • The increased yield for p -iodoaniline to afford 63 (27%) and 47% recovered 33 with NCS (unoptimized) suggests that substrates can be optimized when standard conditions fail (Scheme 6).
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    • The methyl carbamate was available in quantitative yield from the commercial 7-bromotryptamine, whose preparation can be found in ref 13a. An alternative preparation may be found in the Supporting Information
    • The methyl carbamate was available in quantitative yield from the commercial 7-bromotryptamine, whose preparation can be found in ref 13a. An alternative preparation may be found in the Supporting Information.
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    • Kapakahi is the Hawaiian word for twisted
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    • Although no base is added, either DMF or trace dimethylamine may act as a base in this peptide coupling reaction.
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    • 1H NMR to that of the natural source, please see ref 13b. For HMQC, HMBC, and ROESY NMR data for kapakahine F (2), please see the Supporting Information
    • 1H NMR to that of the natural source, please see ref 13b. For HMQC, HMBC, and ROESY NMR data for kapakahine F (2), please see the Supporting Information.
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    • Assays performed by Bristol-Myers Squibb
    • Assays performed by Bristol-Myers Squibb.
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    • Assays performed by the NCI
    • Assays performed by the NCI.
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    • During the review of this manuscript, a synthesis of kapakahine F was reported that proceeded in 19 linear steps and 6.8% overall yield (23 mg produced) from tryptophan:, DOI: 10.1021/ol100672z (published ASAP online Mar 26, 2010)
    • During the review of this manuscript, a synthesis of kapakahine F was reported that proceeded in 19 linear steps and 6.8% overall yield (23 mg produced) from tryptophan: Espejo, V. R. and Rainier, J. D. Org. Lett. 2010, 12, DOI: 10.1021/ol100672z (published ASAP online Mar 26, 2010).
    • (2010) Org. Lett. , vol.12
    • Espejo, V.R.1    Rainier, J.D.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.