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Volumn 12, Issue 22, 2010, Pages 5196-5199

Enantioselective total synthesis of (-)- and (+)-petrosin

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; PETROSIN; QUINOLIZIDINE DERIVATIVE;

EID: 78449299959     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1022257     Document Type: Article
Times cited : (15)

References (30)
  • 10
    • 78449293491 scopus 로고    scopus 로고
    • Enantiomeric excess was determined by HPLC as a TBDPS ether
    • Enantiomeric excess was determined by HPLC as a TBDPS ether.
  • 11
    • 78449303284 scopus 로고    scopus 로고
    • The absolute configuration was determined by conversion of 10 to the previously reported product, (+)-(3 S)- N - tert -butoxycarbonyl-3- hydroxymethyl-piperidine. See Supporting Information for details
    • The absolute configuration was determined by conversion of 10 to the previously reported product, (+)-(3 S)- N-tert -butoxycarbonyl-3-hydroxymethyl- piperidine. See Supporting Information for details.
  • 20
    • 78449272837 scopus 로고    scopus 로고
    • We synthesized 22 from racemic 6 in 7 steps in a similar manner. See Supporting Information for details
    • We synthesized 22 from racemic 6 in 7 steps in a similar manner. See Supporting Information for details.
  • 21
    • 78449273060 scopus 로고    scopus 로고
    • To the best of our knowledge, there is no example of quinolizidine synthesis by aza-Michael reaction using α-substituted enone as a substrate. For an example of quinolizidine synthesis in a similar system, see
    • To the best of our knowledge, there is no example of quinolizidine synthesis by aza-Michael reaction using α-substituted enone as a substrate. For an example of quinolizidine synthesis in a similar system, see
  • 25
    • 78449301056 scopus 로고    scopus 로고
    • The product 24 is presumably a thermodynamic product since this isomer was obtained as a single isomer under the basic conditions with heating (Table 1, entry 2), in which the analogous compound underwent epimerization (ref 14b)
    • The product 24 is presumably a thermodynamic product since this isomer was obtained as a single isomer under the basic conditions with heating (Table 1, entry 2), in which the analogous compound underwent epimerization (ref 14b).
  • 26
    • 78449304249 scopus 로고    scopus 로고
    • 3N. See Supporting Information for details
    • 3N. See Supporting Information for details.
  • 27
    • 78449298845 scopus 로고    scopus 로고
    • When the reaction was performed without p -quinone, a significant decrease in yield (45%) was observed, likely due to isomerization of the terminal C-C double bonds (ref 10)
    • When the reaction was performed without p -quinone, a significant decrease in yield (45%) was observed, likely due to isomerization of the terminal C-C double bonds (ref 10).
  • 28
    • 78449283310 scopus 로고    scopus 로고
    • 3N, a decrease in yield (<60%) was observed
    • 3N, a decrease in yield (<60%) was observed.
  • 29
    • 78449276624 scopus 로고    scopus 로고
    • The optical purity of the synthetic petrosin (>99% ee) was confirmed by Mosher's method for a diol derived from 1, which was prepared by reduction of two carbonyl groups, indicating that epimerization of optically active petrosin did not proceed at all in our case
    • The optical purity of the synthetic petrosin (>99% ee) was confirmed by Mosher's method for a diol derived from 1, which was prepared by reduction of two carbonyl groups, indicating that epimerization of optically active petrosin did not proceed at all in our case.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.