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Volumn , Issue 15, 2008, Pages 2355-2359

Total synthesis of arylomycin A2, a signal peptidase I (SPase I) inhibitor

Author keywords

Antibiotics; Cross coupling; Macrocycles; Palladium; Total synthesis

Indexed keywords

ARYLOMYCIN A2; CYCLOPHANE; ENZYME INHIBITOR; MACROCYCLIC COMPOUND; SIGNAL PEPTIDASE I; UNCLASSIFIED DRUG;

EID: 52949142238     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1078209     Document Type: Article
Times cited : (18)

References (42)
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    • Selected Physical and Spectroscopic Data Compound 10: [α]D25 +86 (c 0.9, MeOH, 1H NMR (300 MHz, MeOD, δ, 7.61 (d, J, 2.0 Hz, 1 H, 7.12 (dd, J, 8.3, 2.0 Hz, 1 H, 6.84 (d, J, 8.3 Hz, 1 H, 5.47 (s, 1 H, 2.66 (s, 3 H, 1.48 (s, 9 H) ppm. HRMS (ES, m/z calcd for C 14H18NO5NaI [M, Na, 430.0127; found: 430.0128. Compound 5: [α]D25 +16(c 1.0, CHCl3, 1H NMR (300 MHz, CDCl 3, 1:1 mixture of retainers, δ, 7.72 and 7.71 (d, J, 2.2 Hz, 1 H, 7.42 and 7.30 (d, J, 2.3 Hz, 1 H, 7.29-7.24 (m, 0.5 H, overlapped with solvent, 7.22 (dd, J, 8.5, 2.2 Hz, 0.5 H, 7.22 (dd, J, 8.5, 2.2 Hz, 0.5 H, 7.10 (dd, J, 8.5, 2.2 Hz, 0.5 H, 6.78 (d, J, 8.5 Hz, 1 H, 6.71 (d, J, 8.5 Hz, 1 H, 6.58-6.32 m, 1 H, 6.54 an
    • - 823.4242; found: 823.4269.
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    • Abbreviations: DEPBT, 3-(diethyloxyphosphoryloxy)-1,2,3-benzotriazin-4 (3H)-one; EDC, 1-[3-(eimethyl-amino)propyl]-3-ethylcarbodiimide; HOBt, N-hydroxybenzotriazole, SPhos, 2-dicyclohexylphosphino-2′, 6′-dimethoxybiphenyl; MOP, diphenylphosphino)-2′-methoxy-1, 1′-binaphtyl; NMP, N-methylpyrolidinone
    • Abbreviations: DEPBT = 3-(diethyloxyphosphoryloxy)-1,2,3-benzotriazin-4 (3H)-one; EDC = 1-[3-(eimethyl-amino)propyl]-3-ethylcarbodiimide; HOBt = N-hydroxybenzotriazole, SPhos = 2-dicyclohexylphosphino-2′, 6′-dimethoxybiphenyl; MOP = (diphenylphosphino)-2′-methoxy-1, 1′-binaphtyl; NMP = N-methylpyrolidinone.
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    • Microwave experiments were conducted using a Discover microwave reactor from CEM. All experiments were performed in sealed tubes (capacity 10 mL) under argon atmosphere. Microwave irradiation of 300 W was used, the temperature being ramped from r.t. to 90°C or 110°C in 1 min. Once this temperature was reached, the reaction mixture was held at 90°C or 110°C for the indicated time.
    • Microwave experiments were conducted using a Discover microwave reactor from CEM. All experiments were performed in sealed tubes (capacity 10 mL) under argon atmosphere. Microwave irradiation of 300 W was used, the temperature being ramped from r.t. to 90°C or 110°C in 1 min. Once this temperature was reached, the reaction mixture was held at 90°C or 110°C for the indicated time.
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    • We synthesized isolauric acid following a Cu-catalyzed coupling of a Grignard reagent with an alkylbromide according to: Cahiez, G, Chaboche, C, Jézéquel, M. Tetrahedron 2000, 56, 2733
    • We synthesized isolauric acid following a Cu-catalyzed coupling of a Grignard reagent with an alkylbromide according to: Cahiez, G.; Chaboche, C.; Jézéquel, M. Tetrahedron 2000, 56, 2733.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.