Research & Faculty

Default Header Image

An asymmetric formal synthesis of fasicularin

TitleAn asymmetric formal synthesis of fasicularin
Publication TypeJournal Article
Year of Publication2005
AuthorsFenster, MDB, Dake, GR
JournalChemistry-a European Journal
Volume11
Pagination639-649
Date PublishedJan
Type of ArticleReview
ISBN Number0947-6539
KeywordsALKALOIDS, ALPHA-HYDROXY EPOXIDES, ASCIDIAN CLAVELINA-CYLINDRICA, BETA-SILOXY ALDEHYDES, CROSS-COUPLING, CROSS-COUPLING REACTION, DIELS-ALDER REACTION, ENANTIOSPECIFIC, EPOXY SILYL ETHERS, MARINE ALKALOID LEPADIFORMINE, REGIOSELECTIVE OLEFIN INSERTION, ring expansion, SEMI-PINACOL REARRANGEMENT, semipinacol rearrangement, spirocycle
Abstract

An asymmetric formal synthesis of fasicularin (1) is described. This natural product, isolated from the extracts of the marine invertebrate Nephteis fasicularis, has shown modest cytotoxicity towards Vero cells. Fasicularin is among only two members of the cylindricine family of natural products, along with lepadiformine (2), to possess a trans A-B ring junction. Key steps of this approach to 1 involve a siloxy-epoxide semipinacol rearrangement of 5 to 6, a B-alkyl Suzuki-Miyaura coupling reaction by using enol trifluoromethanesulfonate 19 and a substrate-directed hydrogenation reaction of 24. This formal synthesis also highlights the difficulty in the incorporation of the thiocyanate functionality present in 1.

URL<Go to ISI>://000226333500017