Issue 7, 1989

Total synthesis of sophorapterocarpan A, maackiain, and anhydropisatin: application of a 1,3-Michael-Claisen annulation to aromatic synthesis

Abstract

A new synthetic route to the pterocarpans using a [3C + 3C] annulation is described. 1,3-Michael-Claisen condensation of α-methylene-γ-butyrolactones with α-sulphur-substituted ketones gives 6-membered rings which have been converted into the pterocarpan framework by aromatization. Sophorapterocarpan A, maackiain, and anhydropisatin have been prepared employing this new aromatic synthesis.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1989, 1219-1224

Total synthesis of sophorapterocarpan A, maackiain, and anhydropisatin: application of a 1,3-Michael-Claisen annulation to aromatic synthesis

Y. Ozaki, K. Mochida and S. Kim, J. Chem. Soc., Perkin Trans. 1, 1989, 1219 DOI: 10.1039/P19890001219

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