Application of the Combined C—H Activation/Cope Rearrangement as a Key Step in the Total Syntheses of the Assigned Structure of (+)-Elisabethadione (V) and a (+)-p-Benzoquinone Natural Product (VI).

ChemInform ◽  
2007 ◽  
Vol 38 (6) ◽  
Author(s):  
Huw M. L. Davies ◽  
Xing Dai
Keyword(s):  
Natural Product ◽  
Cope Rearrangement ◽  
Total Syntheses

scholarly journals Total Syntheses of Pladienolide-Derived Spliceosome Modulators

Molecules ◽  
2021 ◽  
Vol 26 (19) ◽  
pp. 5938
Author(s):  
Jaehoon Sim ◽  
Eunbin Jang ◽  
Hyun Jin Kim ◽  
Hongjun Jeon
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Structural Features ◽  
Synthetic Approach ◽  
Synthetic Analog ◽  
Phase I Clinical Trials ◽  
Total Syntheses ◽  
Naturally Occurring ◽  
Anti Cancer ◽  
Synthetic Approaches

Pladienolides, an emerging class of naturally occurring spliceosome modulators, exhibit interesting structural features, such as highly substituted 12-membered macrocycles and epoxide-containing diene side chains. The potential of pladienolides as anti-cancer agents is confirmed by H3B-8800, a synthetic analog of this natural product class, which is currently under Phase I clinical trials. Since its isolation in 2004 and the first total synthesis in 2007, a dozen total syntheses and synthetic approaches toward the pladienolide class have been reported to date. This review focuses on the eight completed total syntheses of naturally occurring pladienolides or their synthetic analogs, in addition to a synthetic approach to the main framework of the natural product.

Total Syntheses of the Antibacterial Natural Product Abyssomicin C

2006 ◽  
Vol 45 (35) ◽  
pp. 5736-5739 ◽  
Author(s):  
René Peters ◽  
Daniel F. Fischer
Keyword(s):  
Natural Product ◽  
Total Syntheses

Transition metal-promoted biomimetic steps in total syntheses

2014 ◽  
Vol 31 (4) ◽  
pp. 533-549 ◽  
Author(s):  
Xu-Wen Li ◽  
Bastien Nay
Keyword(s):  
Transition Metal ◽  
Transition Metals ◽  
Natural Product ◽  
Natural Product Synthesis ◽  
Total Syntheses

Important biomimetic steps in natural product synthesis have been promoted by transition metals, as exemplified by this beautiful ruthenium-catalyzed rearrangement of an endoperoxide into elysiapyrone A. Such reactions are supposed to occur during the biosynthesis, yet under different catalysis conditions.

Modular total syntheses of mycolactone A/B and its [2H]-isotopologue

2017 ◽  
Vol 15 (36) ◽  
pp. 7518-7522 ◽  
Author(s):  
Sarah Saint-Auret ◽  
Hajer Abdelkafi ◽  
Didier Le Nouen ◽  
Laure Guenin-Macé ◽  
Caroline Demangel ◽  
...  
Keyword(s):  
Natural Product ◽  
Total Syntheses

A new synthetic blueprint of mycolactone A/B is reported, granting access to the natural product and its [2H]-isotopologue.

The Total Syntheses of Phorboxazoles — New Classics in Natural Product Synthesis.

ChemInform ◽  
2003 ◽  
Vol 34 (35) ◽  
Author(s):  
Lars Ole Haustedt ◽  
Ingo V. Hartung ◽  
H. M. R. Hoffmann
Keyword(s):  
Natural Product ◽  
Natural Product Synthesis ◽  
Total Syntheses

scholarly journals The Calyciphylline B-type Alkaloids: Total Syntheses of (–)-Daphlongamine H and (–)-Isodaphlongamine H

2019 ◽  
Author(s):  
Cedric Hugelshofer ◽  
Vignesh Palani ◽  
Richmond Sarpong
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Mannich Reaction ◽  
Biosynthetic Pathway ◽  
Total Syntheses ◽  
Diastereoselective Hydrogenation ◽  
Tricyclic Core ◽  
Synthetic Studies

The first total synthesis of the complex hexacylic Daphniphyllum alkaloid (–)-daphlongamine H in enantioenriched form has been accomplished. Key to the success of the strategy are a complexity-building Mannich reaction, efficient cyclizations, and a highly diastereoselective hydrogenation to assemble multigram quantities of the tricyclic core bearing four contiguous stereocenters. Following construction of the hydro-indene substructure by means of a Pauson–Khand reaction, endgame redox manipulations delivered the natural product. Importantly, the synthetic studies have also given access to (–)-isodaphlongamine H and led to a revision of the reported structure of deoxyisocalyciphylline B, which resulted in the proposal of a modified biosynthetic pathway to the calyciphylline B-type alkaloids.

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