Enantioselective Total Synthesis of (+)-Milnamide A and Evidence of Its Autoxidation to (+)-Milnamide D

Spontaneous oxidation of the marine‐sponge‐derived peptide (+)‐milnamide A (1) to (+)‐milnamide D (2), which is also a natural product, was observed during the total synthesis of 1. The absolute configurations of the structures were determined and are also reported.

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2004-11, Vol.43 (44), p.5951-5954
Main Authors: Liu, Chaomin, Masuno, Makoto N., MacMillan, John B., Molinski, Tadeusz F.
Format: Article
Language:English
Subjects:
carboline
Circular Dichroism
enantioselectivity
Molecular Conformation
natural products
Oligopeptides - chemical synthesis
Oligopeptides - chemistry
Oxidation-Reduction
peptides
Stereoisomerism
total synthesis
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Description
Summary:Spontaneous oxidation of the marine‐sponge‐derived peptide (+)‐milnamide A (1) to (+)‐milnamide D (2), which is also a natural product, was observed during the total synthesis of 1. The absolute configurations of the structures were determined and are also reported.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200461245