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Total Synthesis of (+)‐Madangamine D
Author(s) -
Ballette Roberto,
Pérez Maria,
Proto Stefano,
Amat Mercedes,
Bosch Joan
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201402263
Subject(s) - enantioselective synthesis , total synthesis , enantiomer , alkaloid , stereochemistry , stereoselectivity , chemistry , sponge , absolute configuration , lactam , organic chemistry , catalysis , botany , biology
Madangamines are a group of bioactive marine sponge alkaloids, embodying an unprecedented diazapentacyclic skeletal type. The enantioselective total synthesis of madangamine D has been accomplished, and represents the first total synthesis of an alkaloid of the madangamine group. It involves the stereoselective construction of the diazatricyclic ABC core using a phenylglycinol‐derived lactam as the starting enantiomeric scaffold and the subsequent assembly of the peripheral macrocyclic rings. The synthesis provides, for the first time, a pure sample of madangamine D and confirms the absolute configuration of this alkaloid family.