PubMed 16092865

Referenced in Channelpedia wiki pages of: none

Automatically associated channels: Kv1.3

Title: Enantioselective total synthesis of (-)-candelalide A, a novel blocker of the voltage-gated potassium channel Kv1.3 for an immunosuppressive agent.

Authors: Kazuhiro Watanabe, Katsuhiko Iwasaki, Toshiaki Abe, Munenori Inoue, Kôichi Ohkubo, Takeyuki Suzuki, Tadashi Katoh

Journal, date & volume: Org. Lett., 2005 Aug 18 , 7, 3745-8

PubMed link:

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]