176718-78-8Relevant articles and documents
Total synthesis of (-)-balanol
Miyabe, Hideto,Torieda, Mayumi,Inoue, Kyoko,Tajiri, Kazumi,Kiguchi, Toshiko,Naito, Takeaki
, p. 4397 - 4407 (2007/10/03)
The efficient total synthesis of (-)-balanol, a potent inhibitor of the protein kinase C, is described (-)-Balanol consists of a chiral hexahydroazepine-containing fragment and a benzophenone fragment, both of which were prepared via novel synthetic routes. The hxahydroazepine fragment was prepared in racemic form through either Bu3SnH- or SmI2-promoted radical cyclization of oxime ethers 2ab intramolecularly connected with the formyl group. SmI2-promoted radical cyclization of 2b was found to be particularly successful in the selective synthesis of the seven-membered trans-amino alcohol 8b. Preparation of the enantiomerically pure hexahydroazepine-containing fragment was achieved through the enantioselective enzymatic acetylation of racemic alcohol 9, employing the immobilized lipase from Pseudomonas sp. The benzophenone fragment was prepared in short steps through a biomimetic oxidative anthraquinone ring cleavage starting from commercially available natural chrysophanic acid 15c. This reaction proceeded via [4 + 2]-cycloaddition of single of oxygen to anthracene derivative 17c, followed by Baeyer-Villiger-type rearrangement of the resulting hydroperoxide to afford the benzophenone derivatives 22 and 23.
