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Volumn 9, Issue 4, 2007, Pages 631-634

An Evans-Tishchenko-ring-closing metathesis approach to medium-ring lactones

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; KETONE; LACTONE; OCTALACTIN A; UNCLASSIFIED DRUG;

EID: 33847792405     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062932z     Document Type: Article
Times cited : (34)

References (42)
  • 2
    • 33645364955 scopus 로고    scopus 로고
    • For a comprehensive review of macrolactonizations in the synthesis of natural products, see
    • For a comprehensive review of macrolactonizations in the synthesis of natural products, see: Parenty, A.; Moreau, X.; Campagne, J.-M. Chem. Rev. 2006, 106, 911-939.
    • (2006) Chem. Rev , vol.106 , pp. 911-939
    • Parenty, A.1    Moreau, X.2    Campagne, J.-M.3
  • 12
    • 33847772917 scopus 로고    scopus 로고
    • RCM approaches to the synthesis of 8-membered ring lactones: (a) Mohapatra, D. K.; Yellol, G. S. Arkivoc 2003 (ix), 21-33.
    • RCM approaches to the synthesis of 8-membered ring lactones: (a) Mohapatra, D. K.; Yellol, G. S. Arkivoc 2003 (ix), 21-33.
  • 15
    • 0037159780 scopus 로고    scopus 로고
    • RCM approaches to the synthesis of 9-membered ring lactones: (a) Takahashi, T.; Watanabe, H.; Kitahara, T. Heterocycles 2002, 58, 99-104.
    • RCM approaches to the synthesis of 9-membered ring lactones: (a) Takahashi, T.; Watanabe, H.; Kitahara, T. Heterocycles 2002, 58, 99-104.
  • 17
    • 13844272597 scopus 로고    scopus 로고
    • RCM approaches to the synthesis of 10-membered ring lactones: (a) Kangani, C. O.; Brulckner, A. M.; Curran, D. P. Org. Lett. 2005, 7, 379-382.
    • RCM approaches to the synthesis of 10-membered ring lactones: (a) Kangani, C. O.; Brulckner, A. M.; Curran, D. P. Org. Lett. 2005, 7, 379-382.
  • 26
    • 3543057490 scopus 로고    scopus 로고
    • A preformed Sm(III) catalyst was used to prevent any side reactions between the unsaturated aldehyde and Sm(II): Edmonds, D. J.; Johnston, D.; Procter, D. J. Chem. Rev. 2004, 104, 3371-3403.
    • A preformed Sm(III) catalyst was used to prevent any side reactions between the unsaturated aldehyde and Sm(II): Edmonds, D. J.; Johnston, D.; Procter, D. J. Chem. Rev. 2004, 104, 3371-3403.
  • 30
    • 33847783813 scopus 로고    scopus 로고
    • It was anticipated that the differential protection of fragments 14 and 15 would allow a facile deprotection of the precursor to β-hydroxy ketone 13, making 10b a more attractive target.
    • It was anticipated that the differential protection of fragments 14 and 15 would allow a facile deprotection of the precursor to β-hydroxy ketone 13, making 10b a more attractive target.
  • 33
    • 33847787719 scopus 로고    scopus 로고
    • Silyl protection of 20 was not required as no significant acyl migration was observed with this more sterically demanding substrate.
    • Silyl protection of 20 was not required as no significant acyl migration was observed with this more sterically demanding substrate.
  • 36
    • 0003405157 scopus 로고    scopus 로고
    • 3rd ed, Georg Thieme Verlag: Stuttgart
    • Kocienski, P. J. Protecting Groups, 3rd ed.; Georg Thieme Verlag: Stuttgart, 2004.
    • (2004) Protecting Groups
    • Kocienski, P.J.1
  • 40
    • 33847770564 scopus 로고    scopus 로고
    • Presumably introduction of the C(4) allylic methyl group in 28 (which is absent in 20) renders the desired RCM relatively less favorable; hence, a shift from a 9:1 to 1:1 ratio of products occurs.
    • Presumably introduction of the C(4) allylic methyl group in 28 (which is absent in 20) renders the desired RCM relatively less favorable; hence, a shift from a 9:1 to 1:1 ratio of products occurs.
  • 41
    • 33847770113 scopus 로고    scopus 로고
    • The epoxide stereochemistry in 30 and 31 is assumed on the basis of literature precedent for epoxidation of the related lactones.
    • The epoxide stereochemistry in 30 and 31 is assumed on the basis of literature precedent for epoxidation of the related lactones.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.