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Pure Appl. Chem., 2011, Vol. 83, No. 3, pp. 425-433

http://dx.doi.org/10.1351/PAC-CON-10-09-12

Published online 2011-01-13

Synthetic studies toward the spiroimine unit of the spirolides

Stéphanie M. Guéret and Margaret A. Brimble*

Department of Chemistry, The University of Auckland, 23 Symonds Street, Auckland, New Zealand

Abstract: Synthetic studies toward the spiroimine unit of the spirolide family of shellfish biotoxins are described. Several strategies for introduction of the C7, C29, and C32 stereocenters of the A,E-ring system of the spirolides are described, such as spironitrone formation, Birch reductive alkylation, and asymmetric Diels–Alder cycloadditions.