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Volumn , Issue 36, 2009, Pages 6386-6392

Natural and unnatural A-seco terpenes from pulegone: Synthesis of galbanic acid and marneral revisited

Author keywords

Chiral pool; Microwave chemistry; Mitsunobu etherification; Natural products; Terpenoids

Indexed keywords


EID: 71849086233     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200901021     Document Type: Article
Times cited : (10)

References (45)
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    • During in vitro experiments galbanic acid suppressed the development of platelet aggregation induced by ADP, thrombin, histamine, adrenaline, acetylcholine, and collagen at concentrations of 50, 100, and 200 μg/mL
    • During in vitro experiments galbanic acid suppressed the development of platelet aggregation induced by ADP, thrombin, histamine, adrenaline, acetylcholine, and collagen at concentrations of 50, 100, and 200 μg/mL. M. M. Mansurov, M. S. Martirosov, Farmakol. Toksikol. 1990, 53, 51-53.
    • (1990) Farmakol. Toksikol. , vol.53 , pp. 51-53
    • Mansurov, M.M.1    Martirosov, M.S.2
  • 17
    • 33646124608 scopus 로고    scopus 로고
    • Matsuda et al. named this compound marneral (and its corresponding alcohol 3b marnerol) in recognition of the pioneering work of Marner on iridals. Compound 3 has never been isolated but was hypothesized to be the first carbocyclic precursor in the biosynthesis of iridals
    • Matsuda et al. named this compound marneral (and its corresponding alcohol 3b marnerol) in recognition of the pioneering work of Marner on iridals. Compound 3 has never been isolated but was hypothesized to be the first carbocyclic precursor in the biosynthesis of iridals. Q. Xiong, W. K. Wilson, S. Matsuda, Angew. Chem. Int. Ed. 2006, 45, 1285-1288.
    • (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 1285-1288
    • Xiong, Q.1    Wilson, W.K.2    Matsuda, S.3
  • 25
    • 71849084505 scopus 로고    scopus 로고
    • We thank Professor Giovanni Appendino, Università del Piemonte Orientale, Novara, for supplying natural galbanic acid and for helpful discussion
    • We thank Professor Giovanni Appendino, Università del Piemonte Orientale, Novara, for supplying natural galbanic acid and for helpful discussion.
  • 26
    • 0041904925 scopus 로고    scopus 로고
    • The original assignment made by Bagirov[1a] was later revised by Lee who proposed an alternative structure, reversing the relative configurations at C8 and C9
    • The original assignment made by Bagirov[1a] was later revised by Lee who proposed an alternative structure, reversing the relative configurations at C8 and C9: S.-G. Lee, S. Ryu, J. W. Ahn, Bull. Korean Chem. Soc. 1998, 19, 384-386.
    • (1998) Bull. Korean Chem. Soc. , vol.19 , pp. 384-386
    • Lee, S.-G.1    Ryu, S.2    Ahn, J.W.3
  • 27
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    • The construction of a functionalized six-membered ring by conversion of an allylic alcohol into an allyl-vinyl-substituted ether followed by subsequent Claisen rearrangement was first reported by Ireland et al. in the early eighties
    • The construction of a functionalized six-membered ring by conversion of an allylic alcohol into an allyl-vinyl-substituted ether followed by subsequent Claisen rearrangement was first reported by Ireland et al. in the early eighties: R. E. Ireland, M. D. Varney, J. Org. Chem. 1983, 48, 1829-1833.
    • (1983) J. Org. Chem. , vol.48 , pp. 1829-1833
    • Ireland, R.E.1    Varney, M.D.2
  • 29
    • 0141720171 scopus 로고    scopus 로고
    • The Reymond protocol works perfectly by moving only one carbon atom farther from the neopentylic center (see ref.[12])
    • E. M. Gonzalez-Garcia, J. Grognux, D. Wahler, J.-L. Reymond, Helv. Chim. Acta 2003, 86, 2458-2470. The Reymond protocol works perfectly by moving only one carbon atom farther from the neopentylic center (see ref.[12]).
    • (2003) Helv. Chim. Acta , vol.86 , pp. 2458-2470
    • Gonzalez-Garcia, E.M.1    Grognux, J.2    Wahler, D.3    Reymond, J.-L.4
  • 31
    • 71849118157 scopus 로고    scopus 로고
    • It was anticipated that microwave assistance would be required to achieve ether formation in this highly hindered context. Model studies on previously synthesized i and ii showed that MW irradiation was required to best deal with this concern. (Chemical Equation Presented)
    • It was anticipated that microwave assistance would be required to achieve ether formation in this highly hindered context. Model studies on previously synthesized i and ii showed that MW irradiation was required to best deal with this concern. (Chemical Equation Presented)
  • 32
  • 35
    • 0041565402 scopus 로고    scopus 로고
    • This phenomenon is quite general as numerous examples are reported in the literature
    • This phenomenon is quite general as numerous examples are reported in the literature. G. Mehta, S. R. Kumaran, Tetrahedron Lett. 2003, 44, 7055-7059.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 7055-7059
    • Mehta, G.1    Kumaran, S.R.2
  • 44
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    • A major issue, both in chemical and microbial oxidations, is how to divert oxidation away from the olefin to the desired unactivated sp3 C-H position
    • A major issue, both in chemical and microbial oxidations, is how to divert oxidation away from the olefin to the desired unactivated sp3 C-H position.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.