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Communication | Regular issue | Vol 91, No. 9, 2015, pp.1715-1721
Published online, 11th August, 2015
DOI: 10.3987/COM-15-13288
Synthesis of the Aglycon of Pentalinonside

Nobuhisa Isaka, Saki Kawada, Masaji Ishiguro,* and Minoru Tamiya*

*Chemical Biology Laboratory, Department of Applied Life Sciences, Niigata University of Pharmacy and Applied Life Sciences, 265-1, Higashijima, Niigata 956-8603, Japan

Abstract

The aglycon of pentalinonside (2), a novel seco-pregnane with cage-like DEF-rings, was synthesized. Polyoxygenated DEF-rings were constructed using a known 14,20(16),21(15)-triol derivative via 5-exo-cyclization for the F-ring annulation, followed by C14–21(15) oxidative cleavage and intramolecular acetalization.