Towards a Total Synthesis of Quinocarcin: Diastereoselective Synthesis of Functionalized Azepino[1,2‐b]isoquinolines.

Abstract

Alkaloids U 0600Towards a Total Synthesis of Quinocarcin: Diastereoselective Synthesis of Functionalized Azepino[1,2-b]isoquinolines. -Key structural skeletons (II) and (III) of alkaloid quinocarcin (IV) are prepared by Lewis acid catalyzed hetero-ene reaction of aldehydes (I). The stereoselectivity in the reaction of aldehyde (Ia) is highly dependent on the type of Lewis acid, whereas aldehyde (Ib) affords only diastereomer (IIb) regardless of the Lewis acid. -(KOEPLER, O.; LASCHAT*, S.; BARO, A.; FISCHER, P.; MIEHLICH, B.; HOTFILDER, M.; LE VISEUR, C.; Eur. J. Org.

Total Synthesis of Cryptopleurine and Its Analogues

“…Acetalization of formyl group of 9 under acidic conditions, followed by hydrogenation of pyridine moiety catalyzed by palladium hydroxide under hydrogen atmosphere afforded the desired product 10 . Nucleophilic ring-opening of the epoxide 8 11 with piperidine 10 in the presence of Et 3 Al 12 afforded a mixture of diastereomeric alcohols in high yield. The resulting secondary alcohols were converted into ketone 7 by Swern oxidation.…”