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Synthesis of the Indolic Pentacyclic Core of Manadomanzamine A Following Biogenetically Based Strategies
Author(s) -
Yan LokHang,
Nuhant Philippe,
Sinigaglia Isabelle,
Fromentin Yann,
Marazano Christian,
Delpech Bernard,
Poupon Erwan
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201101133
Subject(s) - chemistry , biomimetic synthesis , sponge , alkaloid , indole test , stereochemistry , indole alkaloid , organic chemistry , botany , biology
Abstract Manadomanzamine A is a complex alkaloid isolated from a marine sponge that shows promising biological activities. A biosynthetic hypothesis is proposed and is used as a guideline for biomimetic approaches to the pentacyclic indole nucleus of manadomanzamine A. The rich chemistry of reactive C 5 units such as glutaconaldehydes or aminopentadienals was exploited towards this end.