Planta Med 2008; 74 - PG39
DOI: 10.1055/s-0028-1084792

A biomimetic approach to manadomanzamine A

LH Yan 1, P Nuhant 2, C Marazano 2, E Poupon 1
  • 1Laboratoire de Pharmacognosie, UMR 8076 BioCIS, Faculté de Pharmacie, Université Paris-Sud 11, 92296 Châtenay-Malabry, France
  • 2Institut de Chimie des Substances Naturelles, CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France

Manadomanzamine A was isolated from a sponge of the genus Acanthostrongylophora (Haploscerida, Petrosidae) and was shown to exhibit interesting antimycobacterial properties [1]. This molecule presents an intriguing synthetic challenge in view of its unprecedented molecular structure. We report the construction of model systems towards a biomimetic approach. Central in our biosynthetic proposals, is the involvement of reactive C3 units related to malonaldehyde [2].

The key-step is the use of substituted aminopentandienals and tryptamine for the assembly of the central core of the target.

1. Peng, J. et al. (2003)J. Am. Chem. Soc. 125: 13382–13386.

2. Ge, C.S. et al. (2006) Eur. J. Org. Chem. 4106–4114.