Model studies on the synthesis of madangamine alkaloids. Assembly of the macrocyclic rings

Stefano Proto; Mercedes Amat; Maria Pérez; Roberto Ballette; Federica Romagnoli; Andrea Mancinelli; Joan Bosch

doi:10.1021/ol301672y

Model studies on the synthesis of madangamine alkaloids. Assembly of the macrocyclic rings

Org Lett. 2012 Aug 3;14(15):3916-9. doi: 10.1021/ol301672y. Epub 2012 Jul 25.

Authors

Stefano Proto¹, Mercedes Amat, Maria Pérez, Roberto Ballette, Federica Romagnoli, Andrea Mancinelli, Joan Bosch

Affiliation

¹ Laboratory of Organic Chemistry, Faculty of Pharmacy, and Institute of Biomedicine (IBUB), University of Barcelona, 08028-Barcelona, Spain.

PMID: 22830949
DOI: 10.1021/ol301672y

Abstract

Using simplified model derivatives, the assembly of the macrocyclic rings of madangamines, including the 13- and 14-membered D rings of madangamines C-E, the all-cis-triunsaturated 15-membered D ring of madangamine A, and the (Z,Z)-unsaturated 11-membered E ring common to madangamines A-E, has been studied.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkaloids / chemical synthesis*
Alkaloids / chemistry
Cyclization
Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
Heterocyclic Compounds, 4 or More Rings / chemistry
Models, Molecular*
Molecular Structure
Stereoisomerism

Substances

Alkaloids
Heterocyclic Compounds, 4 or More Rings
madangamine A