| Title | An asymmetric formal synthesis of fasicularin |
| Publication Type | Journal Article |
| Year of Publication | 2005 |
| Authors | Fenster, MDB, Dake, GR |
| Journal | Chemistry-a European Journal |
| Volume | 11 |
| Pagination | 639-649 |
| Date Published | Jan |
| Type of Article | Review |
| ISBN Number | 0947-6539 |
| Keywords | ALKALOIDS, 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 |
