Abstract
The preparative value of one-pot, multicomponent, sequential Michael-Michael-ring-closure reactions followed by aromatization is illustrated in two ways: (1) by a multi-gram example, and (2) by a total synthesis of juncunol, an unusual vinyldihydrophenanthrene.
Similar content being viewed by others
References
Bamfield P and Gordon P F 1984Chem. Soc. Rev. 13 441
Bhattacharyya J 1980Experimentia 36 27
Bhattacharyya J and Miles D H 1977Tetrahedron Lett.2749
Boger D L and Mullican M D 1984J. Org. Chem. 49 4045
Carvalho C F and Sargent M V 1984J. Chem. Soc, Perkin I 1913
Cossey A L, Gunter M J and Mander L N 1980Tetrahedron Lett. 3309
Danheiser R L and Gee S K 1984J. Org. Chem. 49 1674
Dieter R K and Lin Y J 1985Tetrahedron Lett. 39
Dötz K 1984Angew. Chem. (Int. Ed. Engl.) 23 587
Fisch M H, Flick B H and Anditti J 1973Phytochemistry 12 437
Juneja R K, Sharma S C and Tandon J S 1987Phytochemistry 26 1123
Kende A S and Curren D P 1979J. Am. Chem. Soc. 101 1857
Martin R H and Robinson R S 1943J. Chem. Soc. 491
Marvel C S and Cowan J C 1939J. Am. Chem. Soc. 61 3156
McDonald E and Martin R T 1988Tetrahedron Lett. 4723
Miles D H, Bhattacharyya J, Moody N V, Atwood J C, Black S and Hedin P A 1977J. Am. Chem. Soc. 99 618
Pelletier S W, Moody N V, Bhattacharyya J and Miles D 1978Tetrahedron Lett. 425
Posner G H 1986Chem. Revs. 86 831
Posner G H, Lu S B, Asirvatham E, Silversmith E F and Shulman E M 1986J. Am. Chem. Soc. 108 511
Posner G H, Mallamo J P and Black A Y 1981Tetrahedron 37 3921
Schulz A G and Shen M 1981Tetrahedron Lett. 1775
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Posner, G.H., Canella, K.A. & Silversmith, E.F. One-pot, three-component, sequential Michael-Michael-ring-closure reactions. Annulation of meta-dicarboxylated aromatic rings. Total synthesis of juncunol. Proc. Indian Acad. Sci. (Chem. Sci.) 100, 81–90 (1988). https://doi.org/10.1007/BF02839442
Issue Date:
DOI: https://doi.org/10.1007/BF02839442