Total Synthesis of (±)-Trichodermamide B and of a Putative Biosynthetic Precursor to Aspergillazine A Using an Oxaza-Cope Rearrangement

2008 ◽  
Vol 47 (36) ◽  
pp. 6829-6831 ◽  
Author(s):  
Chong-Dao Lu ◽  
Armen Zakarian
Keyword(s):  
Total Synthesis ◽  
Cope Rearrangement ◽  
Biosynthetic Precursor

scholarly journals Bioinspired Oxidative Cyclization of the Geissoschizine Skeleton for the Enantioselective Total Synthesis of Mavacuran Alkaloids

2019 ◽  
Author(s):  
Maxime Jarret ◽  
Victor Turpin ◽  
Aurélien Tap ◽  
Jean-Francois Gallard ◽  
Cyrille Kouklovsky ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Oxidative Coupling ◽  
Indole Alkaloids ◽  
Oxidative Cyclization ◽  
Total Syntheses ◽  
Enantioselective Total Synthesis ◽  
Biosynthetic Precursor ◽  
Monoterpene Indole Alkaloids ◽  
Coupling Approach

We report the enantioselective total syntheses of mavacurans alkaloids, (+)-taberdivarine H, (+)-16-hydoxymethyl-pleiocarpamine, (+)-16-epi-pleiocarpamine, and their postulated biosynthetic precursor 16-formyl-pleiocarpamine. This family of monoterpene indole alkaloids is a target of choice since some of its members are subunits of intricate bisindole alkaloids such as bipleiophylline. Inspired by the biosynthetic hypothesis, we explored an oxidative coupling approach from the geissoschizine framework to form the N1-C16 bond. Quaternization of the aliphatic nitrogen was key to achieve the oxidative coupling induced by KHMDS/I<sub>2 </sub>since<sub> </sub>it hides the nucleophilicity of the aliphatic nitrogen and locks the required cis conformation.

scholarly journals Aza-Cope Rearrangement−Mannich Cyclizations for the Formation of Complex Tricyclic Amines:  Stereocontrolled Total Synthesis of (±)-Gelsemine

2005 ◽  
Vol 127 (51) ◽  
pp. 18046-18053 ◽  
Author(s):  
William G. Earley ◽  
Jon E. Jacobsen ◽  
Andrew Madin ◽  
G. Patrick Meier ◽  
Christopher J. O'Donnell ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Cope Rearrangement

Sceptrin as a Potential Biosynthetic Precursor to Complex Pyrrole—Imidazole Alkaloids: The Total Synthesis of Ageliferin.

ChemInform ◽  
2004 ◽  
Vol 35 (36) ◽  
Author(s):  
Phil S. Baran ◽  
Daniel P. O'Malley ◽  
Alexandros L. Zografos
Keyword(s):  
Total Synthesis ◽  
Biosynthetic Precursor
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