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

CR Hurt, R Lin, H Rapoport

Index: Hurt, Clarence R.; Lin, Ronghui; Rapoport, Henry Journal of Organic Chemistry, 1999 , vol. 64, # 1 p. 225 - 233

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Citation Number: 39

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 α-amino position was protected with an N-trityl group, ensuring the ...