Work

On the Structure of Palau'amine: Evidence for the Revised Relative Configuration from Chemical Synthesis

Year: 2007

Type: article

Abstract: Hexacyclic congeners 3 and 4 of palau'amine, which incorporate both guanidine functional groups and have the cis configuration of the azabicyclo[3.3.0]octane core, are prepared in 14 steps from cycloadduct 6. Synthetic access to these analogues allows the first direct comparison of NMR data for hexacyclic diguanidine structures having the originally proposed cis-azabicyclo[3.3.0]octane fragment with data for natural alkaloids of the palau'amine family. This comparison provides convincing evidence in favor of the recently proposed structural revision of these marine alkaloids, fully supporting the trans configuration of the central azabicyclo[3.3.0]octane ring system of palau'amine and congeners.

Source: Journal of the American Chemical Society

DOI: 10.1021/ja074939x

Authors: Brian A. Lanman, Larry E. Overman, Ralph Paulini, Nicole S. White

Institution: University of California, Irvine

Language: English

Topic: Advanced Synthetic Organic Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Bundesministerium für Bildung und Forschung, National Heart, Lung, and Blood Institute, National Institute of General Medical Sciences

Awards: G4103734621, Practical Chemical Synthesis of Complex Alkaloids, G5139913449, Synthesis of the Phosphatidylinositol 3-Kinase Inhibitor