179945-11-0Relevant articles and documents
An improved synthesis of (-)-brevisamide, a marine monocyclic ether amide of dinoflagellate origin
Tsutsumi, Ryosuke,Kuranaga, Takefumi,Wright, Jeffrey L.C.,Baden, Daniel G.,Ito, Emiko,Satake, Masayuki,Tachibana, Kazuo
experimental part, p. 6775 - 6782 (2010/10/02)
An improved synthesis of (-)-brevisamide a marine cyclic ether isolated from the red-tide dinoflagellate Karenia brevis was achieved. The ether ring portion was constructed from an unsaturated lactone, which was prepared enantioselectively via an Evans aldol reaction and one-pot lactonization in the presence of excessive base after an Ando reaction. The ether ring and a dienol side chain fragment were connected via Suzuki-Miyaura coupling.
The reaction mechanism of spirocylization and stereoselectivity studies for the calyculin C16-C25 fragment
Rauhala, Vesa,Naettinen, Kalle,Rissanen, Kari,Koskinen, Ari M. P.
, p. 4119 - 4126 (2007/10/03)
The mechanism of the double intramolecular hetero-Michael addition, a key reaction in the planned synthesis of the natural product calyculin C, has been studied by NMR. The cyclization follows Baldwin's rules and proceeds first through a six-membered ring
Synthetic studies on aplyronine A, a potent antitumor substance of marine origin: Stereocontrolled synthesis of the C21-C34 segment
Kigoshi, Hideo,Ojika, Makoto,Suenaga, Kiyotake,Mutou, Tsuyoshi,Hirano, Junko,Sakakura, Akira,Ogawa, Takeshi,Nisiwaki, Masanori,Yamada, Kiyoyuki
, p. 1247 - 1250 (2007/10/02)
The C21-C34 segment 2 of aplyronine A (1), a potent antitumor substance of marine origin, was synthesized enantioselectivity in 25 steps (17% overall yield) from imide 11.