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Volumn 11, Issue 20, 2009, Pages 4532-4535

Progress toward the total synthesis of (±)-actinophyllic Acid

Author keywords

[No Author keywords available]

Indexed keywords

ACETAMIDE DERIVATIVE; ACTINOPHYLLIC ACID; INDOLE ALKALOID;

EID: 70349932331     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901746c     Document Type: Article
Times cited : (49)

References (39)
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    • Importantly, bromo diene 8 was produced in 60%-80% yield with exclusive frans-olefin selectivity under these reaction conditions
    • Importantly, bromo diene 8 was produced in 60%-80% yield with exclusive frans-olefin selectivity under these reaction conditions.
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    • Amine displacement of homoallylic dienyl bromide was adapted from
    • Amine displacement of homoallylic dienyl bromide was adapted from: Arnold, H.; Overman. L. E.; Sharp, M. J.; Witschel, M. C. Org. Synth. 1992, 70, 111-118.
    • (1992) Org. Synth. , vol.70 , pp. 111-118
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    • For studies on the cyclopropanation of diazoacetamides. see: (a) Doyle, M. P.: Eismont. M. Y.; Protopopova, M. N.; Kwan, M. M. Y.
    • For studies on the cyclopropanation of diazoacetamides. see: (a) Doyle, M. P.: Eismont. M. Y.; Protopopova, M. N.; Kwan, M. M. Y. Tetrahedron 1994, 50, 1665-1674.
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    • note
    • Under these conditions only minimal quantities of side products were observed.
  • 22
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    • note
    • These conditions remain unoptimized, and current efforts are focusing on both improving efficiency and utilizing chiral metal catalysts to induce asymmetry.
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    • For some examples of enoxysilane-mediated divinylcyclopropane rearrangement in the synthesis of functionalized cycloheptene rings, see: (a)
    • For some examples of enoxysilane-mediated divinylcyclopropane rearrangement in the synthesis of functionalized cycloheptene rings, see: (a) Piers, E.: Burmeister, M. S.: Reissig. H.-U. Can. J. Chem. 1986, 64. 180-187.
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    • note
    • Initial attempts to employ Phenylhydrazine hydrochloride in the Fischer indolization reaction of substrate 15 led to mixtures of products, which arose from non-deprotected and deprotection of the silyl ether.
  • 35
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    • Attempts to condense Phenylhydrazine with ketone 15 under either neutral or protic acid conditions provided only low conversions to the desired hydrazone 19.
    • Attempts to condense Phenylhydrazine with ketone 15 under either neutral or protic acid conditions provided only low conversions to the desired hydrazone 19.
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    • For examples of the use of Sc(OTf)3 as a Lewis acid activator for aldehydes in the presence of hydrazines, see: (a)
    • For examples of the use of Sc(OTf)3 as a Lewis acid activator for aldehydes in the presence of hydrazines, see: (a) Furrow. M. E.; Myers, A. G. J. Am. Chem. Soc. 2004, 126, 5436-5445.
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    • 1H NMR analysis of the unpurified reaction mixture. Isolation yields of 19 typically ranged between 84%-97% yield
    • 1H NMR analysis of the unpurified reaction mixture. Isolation yields of 19 typically ranged between 84%-97% yield,
  • 39
    • 70349934612 scopus 로고    scopus 로고
    • The configuration of hydrazone 19 (i.e., E-hydrazone vs. Zhydrazone) could not be determined by NMR
    • The configuration of hydrazone 19 (i.e., E-hydrazone vs. Zhydrazone) could not be determined by NMR.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.