Enantioselective Total Synthesis of (−)-Candelalide A, a Novel Blocker of the Voltage-Gated Potassium Channel Kv1.3 for an Immunosuppressive Agent
Organic Letters2005Vol. 7(17), pp. 3745–3748
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Kazuhiro Watanabe, Katsuhiko Iwasaki, Toshiaki Abe, Munenori Inoue, K. Ohkubo, Takeyuki Suzuki, Tadashi Katoh
Abstract
A convergent route to (-)-candelalide A involved the union of a trans-decalin portion (AB ring) and a gamma-pyrone moiety through the C16-C3' bond to assemble the whole carbon framework and subsequent formation of the dihydropyran ring (C ring) as the crucial steps. A strategic [2,3]-Wittig rearrangement was employed for establishing the stereogenic center at C9 and an exo-methylene function at C8 present in the decalin portion. [reaction: see text]
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