Novel Approach to the Lundurine Alkaloids: Synthesis of the Tetracyclic Core

Abstract

The tetracyclic core of the lundurine family of alkaloids has been synthesized by a novel approach that features a double ring closing olefin metathesis to form the five-and eight-membered rings.

Synthetic Studies toward Lapidilectine-Type Kopsia Alkaloids

“…4 The most advanced approach, which arrives at the tetracyclic core of lundurine using creative ring closing metathesis reactions, was recently reported by Martin and coworkers. 5 …”

“…4 The most advanced approach, which arrives at the tetracyclic core of lundurine using creative ring closing metathesis reactions, was recently reported by Martin and co-workers. 5 In addition, an elegant total synthesis of lapidilectine B (1) was achieved by Pearson and co-workers in 2001 and featured an inventive use of a 2-azaallyllithium ion in a [3 þ 2] cycloaddition. 6 To date, no synthetic efforts have been reported toward the tenuisines 7 or grandilodines.…”

“…A majority of the synthetic efforts aimed at these compounds have been focused on the lundurine class of molecules . The most advanced approach, which arrives at the tetracyclic core of lundurine using creative ring closing metathesis reactions, was recently reported by Martin and co-workers …”