title: Total synthesis of (-)-kaitocephalin.
abstract: (-)-Kaitocephalin has been synthesized. With the C9 stereocenter from Garner's aldehyde, the C4 quaternary carbon was installed by the desymmetrization of the Cbz-protected serinol. The remaining stereogenic centers were generated through mercuriocyclization, epoxidation and regioselective epoxide opening, in which the quaternary carbon most likely played crucial roles in the stereoinduction.
authors: MIRC, Department of Chemistry, KAIST, Daejeon 305-701, Korea.
authors: Wonchul
authors: W
authors: Lee
authors: Joo-Hack
authors: JH
authors: Youn
authors: Sung Ho
authors: SH
authors: Kang
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D003500:Cyclization; D004852:Epoxy Compounds / Q000737:chemistry; D011412:Propanolamines / Q000737:chemistry; D011409:Propylene Glycols / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D004852:Epoxy Compounds; D011412:Propanolamines; D011409:Propylene Glycols; D011758:Pyrroles; C442421:kaitocephalin; C072422:serinol