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Volumn 54, Issue 3, 2015, Pages 1011-1015

Total syntheses of (-)-huperzine Q and (+)-lycopladines B and C

Author keywords

Alkaloids; Epoxyamines; Metathesis; Natural products; Total synthesis

Indexed keywords

ALKALOIDS; CRYSTAL STRUCTURE;

EID: 84920861282     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201409503     Document Type: Article
Times cited : (52)

References (81)
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    • note
    • (R)-8 was prepared in four steps through a lipase-catalyzed kinetic resolution from the commercially available 3,5-dioxocyclohexanecarboxylic acid; see the Supporting Information for details.
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    • note
    • Iodoaldehyde 9 was prepared in two steps from commercially available 4-aminobutan-1-ol; see Ref. [2q].
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    • note
    • Control experiments showed that the reaction did not proceed at ambient temperature in the absence of ethylene (1 atm), whereas in the presence of ethylene (1 atm), 23% yield was obtained after 22 hours at room temperature.
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    • The ratio of 5 was determined by 2D NMR spectroscopy, and the epimerization process could proceed further by prolonging the reaction time to afford 5 with a 1:1.3 ratio (α/β) after 19 h.
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    • Control experiments showed that 5 did not react with epoxidation reagents, such as meta-chloroperoxybenzoic acid or oxone, to afford epoxyamine 23.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.