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Volumn 75, Issue 1, 2010, Pages 30-43

Perylenequinone natural products: Total syntheses of the diastereomers (+)-phleichrome and (+)-calphostin D by assembly of centrochiral and axial chiral fragments

Author keywords

[No Author keywords available]

Indexed keywords

AXIAL CHIRALITY; CERCOSPORIN; CHEMICAL EQUATIONS; CONVERGENT SYNTHESIS; DIASTEREOMERS; ENANTIOPURE; ENANTIOSELECTIVE; NATURAL PRODUCTS; PHLEICHROME; TOTAL SYNTHESIS;

EID: 73449142824     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901384h     Document Type: Article
Times cited : (36)

References (104)
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    • In all of the prior approaches the C7-stereochemistry was generated first and was followed by a diastereoselective coupling (moderate selectivity) of the chiral naphthalene. Additionally, the predominant diastereomer does not generally correspond to the expected calphostin array, although it does match that needed for phleichrome
    • In all of the prior approaches the C7-stereochemistry was generated first and was followed by a diastereoselective coupling (moderate selectivity) of the chiral naphthalene. Additionally, the predominant diastereomer does not generally correspond to the expected calphostin array, although it does match that needed for phleichrome.
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    • The next paper in this series describes the further evolution of the biscuprates for the cercosporin synthesis. Morgan, B. J, Mulrooney, C.;Kozlowski,M. C. J. Org. Chem. 2010, 75 DOI: 10.1021/jo9013854
    • The next paper in this series describes the further evolution of the biscuprates for the cercosporin synthesis. Morgan, B. J.; Mulrooney, C.;Kozlowski,M. C. J. Org. Chem. 2010, 75 (DOI: 10.1021/jo9013854).
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    • A C2,C2′-bis-isopropyl ether was utilized in the epoxide opening in the first-generation synthesis of cercosporin 3, which is detailed in the next paper of this series (DOI: 10.1021/jo9013854).
    • A C2,C2′-bis-isopropyl ether was utilized in the epoxide opening in the first-generation synthesis of cercosporin 3, which is detailed in the next paper of this series (DOI: 10.1021/jo9013854).
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    • Protic acid protocol: (a) Horper, W.; Marner, F.-J. Phytochemistry 1996, 41, 451. Copper/quinoline protocol:
    • Protic acid protocol: (a) Horper, W.; Marner, F.-J. Phytochemistry 1996, 41, 451. Copper/quinoline protocol:
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    • Broka in ref 6a reported long reaction times (3 d) in cleaving TBDPS ethers (present in the C7,C7′-substitution) of a biaryl similar to 71. In addition, the oxidative cyclization to the perylenequinone stalled at the hydroperylenequinone when the TBDPS groups were present.
    • Broka in ref 6a reported long reaction times (3 d) in cleaving TBDPS ethers (present in the C7,C7′-substitution) of a biaryl similar to 71. In addition, the oxidative cyclization to the perylenequinone stalled at the hydroperylenequinone when the TBDPS groups were present.
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    • For further details on the optimization of the palladium-catalyzed O-arylation and the rhodium-mediated decarbonylation, see the next paper in this series (DOI: 10.1021/jo9013854).
    • For further details on the optimization of the palladium-catalyzed O-arylation and the rhodium-mediated decarbonylation, see the next paper in this series (DOI: 10.1021/jo9013854).
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    • For further details on the sensitivity of different functional groups to PIFA, see the next paper in this series DOI: 10.1021/jo9013854
    • For further details on the sensitivity of different functional groups to PIFA, see the next paper in this series (DOI: 10.1021/jo9013854).
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    • See Scheme 16 in the preceding paper of this series: Mulrooney, C.; Morgan, B. J.; Li, X.; Kozlowski, M. C. J. Org. Chem. 2010, 75 (DOI: 10.1021/jo9013832).
    • See Scheme 16 in the preceding paper of this series: Mulrooney, C.; Morgan, B. J.; Li, X.; Kozlowski, M. C. J. Org. Chem. 2010, 75 (DOI: 10.1021/jo9013832).
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.