메뉴 건너뛰기




Volumn 10, Issue 13, 2008, Pages 2853-2856

Total synthesis and structural confirmation of ent-galbanic acid and marneral

Author keywords

[No Author keywords available]

Indexed keywords

COUMARIN DERIVATIVE; GALBANIC ACID; MARNERAL; TRITERPENE;

EID: 51649117595     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8010216     Document Type: Article
Times cited : (14)

References (32)
  • 1
    • 59949086928 scopus 로고    scopus 로고
    • Structure and stereochemistry of galbanic acid from galbanum: Bagirov, V. Y.; Scheichenko, V. I.; Veselovskaya, N. V.; Sklyar, Y. E.; Savina, A. A.; Kir'yanova, I. A. Khim. Prir. Soedin. 1980, 16, 620-623.
    • Structure and stereochemistry of galbanic acid from galbanum: Bagirov, V. Y.; Scheichenko, V. I.; Veselovskaya, N. V.; Sklyar, Y. E.; Savina, A. A.; Kir'yanova, I. A. Khim. Prir. Soedin. 1980, 16, 620-623.
  • 2
    • 0028010457 scopus 로고    scopus 로고
    • Isolation from asafetida: Appendino, G.; Tagliapetra, S.; Nano, G. M.; Jakupovic, J. Phytochemistry 1994, 35, 183-186.
    • (a) Isolation from asafetida: Appendino, G.; Tagliapetra, S.; Nano, G. M.; Jakupovic, J. Phytochemistry 1994, 35, 183-186.
  • 10
    • 59949096335 scopus 로고    scopus 로고
    • The three stereogenic centres of galbanic acid are contiguous, with the central one being tetrasubstituted. Within this structural context, it is difficult to translate dipolar interactions into a configurational assignment
    • The three stereogenic centres of galbanic acid are contiguous, with the central one being tetrasubstituted. Within this structural context, it is difficult to translate dipolar interactions into a configurational assignment.
  • 11
    • 0000638706 scopus 로고    scopus 로고
    • Matsuda et al, see ref 11 named this compound Marneral (and its corresponding alcohol 33 Marnerol) in recognition of the pioneering work of Marner on iridals. 2 has never been isolated but was hypothesized to be the first carbocyclic precursor in the biosynthesis of iridals, a) Marner, F.-J, Krick, W, Gellrich, B, Jaenicke, L, Winter, W. J. Org. Chem. 1982, 47, 2531-2538
    • Matsuda et al. (see ref 11) named this compound Marneral (and its corresponding alcohol 33 Marnerol) in recognition of the pioneering work of Marner on iridals. 2 has never been isolated but was hypothesized to be the first carbocyclic precursor in the biosynthesis of iridals. (a) Marner, F.-J.; Krick, W.; Gellrich, B.; Jaenicke, L.; Winter, W. J. Org. Chem. 1982, 47, 2531-2538.
  • 18
    • 20444395445 scopus 로고    scopus 로고
    • 2O, 3 h at 138 °C: Dams, I.; Bialonska, A.; Ciunik, Z.; Wawrzenczyk, C. Tetrahedron: Asymmetry 2005, 16, 2087-2097.
    • 2O, 3 h at 138 °C: Dams, I.; Bialonska, A.; Ciunik, Z.; Wawrzenczyk, C. Tetrahedron: Asymmetry 2005, 16, 2087-2097.
  • 21
    • 0039538231 scopus 로고
    • For closely related Claisen rearrangements, see
    • For closely related Claisen rearrangements, see: Ireland, R. E.; Varney, M. D. J. Org. Chem. 1983, 48, 1829-1833.
    • (1983) J. Org. Chem , vol.48 , pp. 1829-1833
    • Ireland, R.E.1    Varney, M.D.2
  • 25
    • 59949085260 scopus 로고    scopus 로고
    • 3)), thus establishing the absolute configuration of galbanic acid as (8S), (9S), (10S).
    • 3)), thus establishing the absolute configuration of galbanic acid as (8S), (9S), (10S).
  • 32
    • 59949089450 scopus 로고    scopus 로고
    • Six-membered rings can adopt various conformations, while a shortage of functional groups causes extensive signal overlapping
    • Six-membered rings can adopt various conformations, while a shortage of functional groups causes extensive signal overlapping.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.