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Volumn 5, Issue 8, 2010, Pages 1902-1910

Total synthesis, assignment of the absolute stereochemistry, and structure-activity relationship studies of subglutinols A and B

Author keywords

Immunosuppressive agents; Nucleophilic substitution; Reductive deoxygenation; Tandem reactions; Total synthesis

Indexed keywords

DEOXYGENATIONS; IMMUNOSUPPRESSIVE AGENT; NUCLEOPHILIC SUBSTITUTIONS; TANDEM REACTION; TOTAL SYNTHESIS;

EID: 77955205246     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.201000147     Document Type: Article
Times cited : (27)

References (57)
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    • references therein
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    • N2' alkylation of phosphate 28 b or the corresponding allyl halide Cl or Br with Zn-homoenolate was not successful due to low yield <20% and regioselectivity <1:1. For the Zn-homoenolate, see
    • N2' alkylation of phosphate 28 b or the corresponding allyl halide (Cl or Br) with Zn-homoenolate was not successful due to low yield (<20%) and regioselectivity (<1:1). For the Zn-homoenolate, see: E. Nakamura, S. Aoki, K. Sekiya, H. Oahino, I. Kuwajima, J. Am. Chem. Soc. 1987, 109, 8056-8066.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 8056-8066
    • Nakamura, E.1    Aoki, S.2    Sekiya, K.3    Oahino, H.4    Kuwajima, I.5
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    • 2, 30b' was formed as the major product
    • 2, 30b' was formed as the major product.
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    • For an extensive discussion about the effects of reaction temperature and solvent on CuI-mediated Grignard reactions, see: a
    • For an extensive discussion about the effects of reaction temperature and solvent on CuI-mediated Grignard reactions, see: a) J. E. Blackvall, M. Sellen, J. Chem. Soc. Chem. Commun. 1987, 827-829;
    • (1987) J. Chem. Soc. Chem. Commun. , pp. 827-829
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    • It is noteworthy that when we used 1, 3-dioxolane instead of 1, 3-dithiane as a carbonyl protecting group, the epimerization of C12 was observed during acid-or Pd-mediated deprotection of the 1, 3-dioxolane group
    • It is noteworthy that when we used 1, 3-dioxolane instead of 1, 3-dithiane as a carbonyl protecting group, the epimerization of C12 was observed during acid-or Pd-mediated deprotection of the 1, 3-dioxolane group.
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    • 3, and DMSO
    • 3, and DMSO.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.