Jolkinolide D pharmacophore: synthesis and reaction with amino acids, nucleosides, and DNA

Sakakura, Akira; Takayanagi, Yui; Kigoshi, Hideo

doi:10.1016/s0040-4039(02)01195-4

Cited by 8 publications

(1 citation statement)

References 9 publications

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“…It was also observed that simple amines were taken up by the reactive alkene under neutral conditions, as were alcohols (presumably alkoxides) under basic conditions . With a large supply of FR182877 in hand, we elected to study the reaction of its strained bridgehead double bond with a variety of nucleophiles . Table shows the results of our reactivity study, which clearly indicate that this strained and reactive site cleanly reacts with amines, thiols, and even imidazole.…”

Section: Resultsmentioning

confidence: 99%

An Enantioselective Synthesis of FR182877 Provides a Chemical Rationalization of Its Structure and Affords Multigram Quantities of Its Direct Precursor

et al. 2003

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The evolution of a strategy culminating in an efficient, enantioselective synthesis of the potent microtubule-stabilizing agent FR182877 is described. Guided by a proposed biogenesis of this complex natural product, a solution emerged that involved the first reported example of a double transannular Diels-Alder reaction to fashion the key elements of its hexacyclic structure. This pivotal transformation creates a complex pentacycle from a 19-membered macrocyclic pentaene, forming seven new stereogenic centers in a fully diastereocontrolled fashion. The efficiency of the approach ultimately enabled the preparation of multigram quantities of the direct precursor of FR182877 for conversion to the relatively unstable natural product when required. The reactivity of the strained, bridgehead olefin of this secondary metabolite with biologically relevant nucleophiles is also described.

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Section: Resultsmentioning

confidence: 99%