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Volumn 7, Issue 15, 2005, Pages 3247-3250

Total synthesis of the neotropical poison-frog alkaloid (-)-205B

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ALKALOID ( ) 205B; ALKALOID (-)-205B; FUSED HETEROCYCLIC RINGS;

EID: 23044510479     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0510264     Document Type: Article
Times cited : (75)

References (30)
  • 6
    • 0031849499 scopus 로고    scopus 로고
    • The known piperidone was prepared in five steps and 35% overall yield from 4-methoxyphenylmethylhex-5-enoate; see: Hodgkinson, T. J.; Shipman, M. Synthesis 1998, 1141.
    • (1998) Synthesis , pp. 1141
    • Hodgkinson, T.J.1    Shipman, M.2
  • 17
    • 0000178458 scopus 로고
    • (b) Chattopadhyay, S.; Mamdapur, V. R.; Chadha, M. S. Tetrahedron 1990, 46, 3667. Aldehyde (-)-10 was prepared in four steps and 95% overall yield from commercially available ethyl (S)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-propenoate (i): see the Supporting Information for details.
    • (1990) Tetrahedron , vol.46 , pp. 3667
    • Chattopadhyay, S.1    Mamdapur, V.R.2    Chadha, M.S.3
  • 20
    • 23044509792 scopus 로고    scopus 로고
    • note
    • In this case, use of HMPA or DMPU as cosolvents to trigger the Brook rearrangement resulted in poor yield (<10%).
  • 27
    • 23044452702 scopus 로고    scopus 로고
    • note
    • Hydrolysis at room temperature for 12 h led to a mixture (ca. 1:1) of aldehydes.
  • 28
    • 23044451933 scopus 로고    scopus 로고
    • see ref 3
    • The stereochemistry at the newly formed position in (+)-16 was later confirmed by comparison of the NMR data of (-)-19 with those of known (+)-19; see ref 3.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.