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Total Synthesis of 19-Nordigitoxigenin, An Antiaroside Y Aglycon
Taishi Matsumura1, Toshio Nishikawa1, Atsuo Nakazaki1,2
1Graduate School of Bioagricultural Sciences, Nagoya University Furo-cho, Chikusa, Nagoya 464-8601, Japan.
Abstract:
The first total synthesis of 19-nordigitoxigenin, an aglycon of antiroside Y, has been achieved. The key steps of our synthesis are (i) construction of the 19-norsteroid ring system via a Mizoroki-Heck reaction between a bromoanisole corresponding to the A-ring and cyclic alkene incorporating the CD-rings, followed by a Friedel-Crafts-type cyclodehydration, and (ii) incorporation of the butenolide moiety at C17 via a silyl-tethered radical cyclization and subsequent ozone oxidation.
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