ChemInform Abstract: Synthesis of (.+-.)-Cylindricines A, D, and E.

✍ Scribed by B. B. SNIDER; T. LIU

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 34 KB
• Volume: 28
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199751235

✦ Synopsis

Synthesis of (±)-Cylindricines A, D, and E.

-The first synthesis of the title compound cylindricine A (XIIa) is accomplished by an efficient route using a double Michael reaction to construct the quinolinone and a radical cyclization to prepare the ( chloromethyl)pyrrolidine. Cyclization of the N-chloropiperidinone (X) and treatment of the crude mixture of (XI) and (XIIa) with NaOMe in MeOH gives 32% of cylindricine D (XIIb) together with 35% of the corresponding epi-cylindricine. Acetylation of (XIIa) affords cylindricine E (XIIc). -(SNIDER, B.