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Volumn 66, Issue 33, 2010, Pages 6546-6549

Synthesis of E-deoxypukalide, and its biomimetic conversion into deoxypseudopterolide by photochemical ring contraction involving a 1,3-allylic shift

Author keywords

1,3 Allylic shift, 1,3 Sigmatropic rearrangement; Deoxypseudopterolide; E Deoxypukalide; Octocorals; Photochemical ring contraction

Indexed keywords

ALLYL COMPOUND; DEOXYPSEUDOPTEROLIDE; DITERPENE; E DEOXYPUKALIDE; NATURAL PRODUCT; UNCLASSIFIED DRUG;

EID: 77955659950     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.04.001     Document Type: Article
Times cited : (15)

References (31)
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    • note
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    • Kallolide A (8) was first isolated from Pseudopterogorgia kallos; see
    • Kallolide A (8) was first isolated from Pseudopterogorgia kallos; see: S.A. Look, M.T. Burch, W. Fenical, Q. Zheng, and J. Clardy J. Org. Chem. 50 1985 5741 5746
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    • For total syntheses of the pseudopteranes gorgiacerone, kallolide A and kallolide B, which were not based on biosynthesis considerations, see
    • For total syntheses of the pseudopteranes gorgiacerone, kallolide A and kallolide B, which were not based on biosynthesis considerations, see: (a) L.A. Paquette, A.M. Doherty, and C.M. Rayner J. Am. Chem. Soc. 114 1992 3910 3926
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    • 0035977211 scopus 로고    scopus 로고
    • For independent syntheses of the enantiomer of natural Z-deoxypukalide see
    • For independent syntheses of the enantiomer of natural Z-deoxypukalide see: J.A. Marshall, and E.A.V. Devender J. Org. Chem. 66 2001 8037 8041
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    • For early, fundamental studies of the stereochemistry of photochemical 1, 3-allylic shifts see
    • For early, fundamental studies of the stereochemistry of photochemical 1, 3-allylic shifts see: R.C. Cookson, J. Hudec, and M. Sharma J. Chem. Soc., Chem. Commun. 1971 107 108
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    • For some recent, relevant discussion see
    • For some recent, relevant discussion see: G. Pattenden, and J.M. Winne Tetrahedron Lett. 50 2009 7310 7313
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    • Pattenden, G.1    Winne, J.M.2
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    • For a recent study of the synthesis of Δ7,8-double bonds in furanocembranes with the E-configuration see
    • For a recent study of the synthesis of Δ7,8-double bonds in furanocembranes with the E-configuration see: T. Gaich, H. Weinstabl, and J. Mulzer Synlett 2009 1357 1366
    • (2009) Synlett , pp. 1357-1366
    • Gaich, T.1    Weinstabl, H.2    Mulzer, J.3
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    • For a photochemical 1,3-sigmatropic migration involving the 2-hexenyl side chain in the γ-pyrone-based natural product tridachiahydropyrone found in molluscs, leading to a positional isomer (which may also be present in nature), see
    • For a photochemical 1,3-sigmatropic migration involving the 2-hexenyl side chain in the γ-pyrone-based natural product tridachiahydropyrone found in molluscs, leading to a positional isomer (which may also be present in nature), see: P. Sharma, B. Lygo, W. Lewis, and J.E. Moses J. Am. Chem. Soc. 131 2009 5966 5972
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.