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Volumn 103, Issue 9, 2003, Pages 3753-3786

Microtubule-stabilizing marine metabolite laulimalide and its derivatives: Synthetic approaches and antitumor activity

Author keywords

[No Author keywords available]

Indexed keywords

ANTITUMOR ACTIVITY; EPOXIDES; MACROCYCLIZATION; MARINE METABOLITE LAULIMALIDE; OLEFINATION;

EID: 0141508044     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr940368c     Document Type: Article
Times cited : (81)

References (242)
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    • note
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    • For additional use in laulimalide synthesis, see: Schemes 11, 13, 24, and 45
    • (b) Rutjes, F. P. J. T.; Kooistra, T. M.; Schoemaker, H. E. Synlett 1998, 192. For additional use in laulimalide synthesis, see: Schemes 11, 13, 24, and 45.
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    • (1985) Asymmetric Synthesis , vol.5 , pp. 193
    • Rossiter, B.E.1
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    • note
    • For closely related approaches to the external dihydropyran fragment, see Schemes 8, 15, 46, 47, and 53.
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    • note
    • 49 and was assumed to occur through a reversible Michael addition of nucleophilic reagents to the active ester intermediate.
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    • For recent applications of the Julia-Kocienski protocol in natural product syntheses, see: (a) Smith, A. B., III; Wan, Z. J. Org. Chem. 2000, 65, 3738 and references therein.
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    • For the clean conversion of a bis-homoallylic alcohol derived from diepoxide 110 to the corresponding cyclooctene derivative by RCM, see: Gravier-Pelletier, C.; Andriuzzi, O.; Le Merrer, Y. Tetrahedron Lett. 2002, 43, 245.
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    • note
    • The acylating agent was prepared from commercially available methyl ester by means of enzymatic hydrolysis with PLE (Fluka 46058) and subsequent reaction of the acid with oxalyl chloride.
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    • For extensive studies on the mechanism and origin of stereoselective opening of chiral dioxane acetals and for leading references, see: Denmark, S. E.; Willson, T. M.; Almstead, N. G. J. Am. Chem. Soc. 1989, 111, 9258.
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    • note
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  • 207
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    • note
    • For previous reports on citronellal-based syntheses of laulimalide fragments, see: Schemes 45, 48, and 49.
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    • note
    • 16b
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    • For an analogous anti-selective reduction with zinc borohydride, see Scheme 22.
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    • note
    • A similar C-propargylation was performed by Williams (cf. Scheme 38).
  • 225
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    • note
    • For additional involvement of 213 in the synthesis of laulimalide fragments, see Schemes 34, 48, and 49.
  • 231
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    • note
    • 20, see: Schemes 40 and 43.
  • 242
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    • note
    • For an analogous approach in Crimmins' total synthesis, see: Scheme 35.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.