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.

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.

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.

scholarly journals Recent Advance of Domino Michael Reaction in Natural Product Synthesis

2021 ◽  
Vol 16 (10) ◽  
pp. 1934578X2110498
Author(s):  
Hisahiro Hagiwara
Keyword(s):  
Natural Products ◽  
Natural Product ◽  
Michael Reaction ◽  
Natural Product Synthesis ◽  
Total Syntheses ◽  
Michael Reactions ◽  
Recent Advances ◽  
Key Steps ◽  
Related Compounds

Recent advances in the total syntheses of cyclic natural products and related compounds from 2005 to 2021, which employ domino Michael reactions as key steps, have been reviewed, focusing mainly on the domino Michael reactions catalyzed by organocatalysts.

scholarly journals Evolution of Pauson-Khand Reaction: Strategic Applications in Total Syntheses of Architecturally Complex Natural Products (2016–2020)

Catalysts ◽  
2020 ◽  
Vol 10 (10) ◽  
pp. 1199
Author(s):  
Sijia Chen ◽  
Chongguo Jiang ◽  
Nan Zheng ◽  
Zhen Yang ◽  
Lili Shi
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
Organic Synthesis ◽  
Total Syntheses

Metal-mediated cyclizations are important transformations in a natural product total synthesis. The Pauson-Khand reaction, particularly powerful for establishing cyclopentenone-containing structures, is distinguished as one of the most attractive annulation processes routinely employed in synthesis campaigns. This review covers Co, Rh, and Pd catalyzed Pauson-Khand reaction and summarizes its strategic applications in total syntheses of structurally complex natural products in the last five years. Additionally, the hetero-Pauson-Khand reaction in the synthesis of heterocycles will also be discussed. Focusing on the panorama of organic synthesis, this review highlights the strategically developed Pauson-Khand reaction in fulfilling total synthetic tasks and its synthetic attractiveness is aimed to be illustrated.

Sign in / Sign up

Export Citation Format

Share Document