title: Enantiospecific Synthesis of (R)-4-Amino-5-oxo-1,3,4,5-tetrahydrobenz[cd]indole, an Advanced Intermediate Containing the Tricyclic Core of the Ergots.
abstract: We report a new strategy for the enantiospecific synthesis of (R)-4-amino-5-oxo-1,3,4,5-tetrahydrobenz[cd]indole. This compound is an advanced intermediate which contains the tricyclic core of many of the tetracyclic ergot alkaloids. Our method involves the initial synthesis of D-4-bromotryptophan from the coupling of an indolyllithium species with a masked serinal. The alpha-amino position was protected with an N-trityl group, ensuring the enantiomeric integrity of this position during the ensuing organometallic cyclization reaction. Stabilization of the tricycle was accomplished by protecting the indole nitrogen with a BOC group or by reducing the alpha-amino ketone to the corresponding beta-amino alcohol.
authors.affiliation: Department of Chemistry, University of California, Berkeley, California 94720.
authors.forename: Clarence R.
authors.initials: CR
authors.lastname: Hurt
authors.forename: Ronghui
authors.initials: R
authors.lastname: Lin
authors.forename: Henry
authors.initials: H
authors.lastname: Rapoport