Enantioselective Total Syntheses of Several Bioactive Natural Products Based on the Development of Practical Asymmetric Catalysis

ChemInform ◽  
2005 ◽  
Vol 36 (8) ◽  
Author(s):  
Takashi Ohshima
Keyword(s):  
Natural Products ◽  
Asymmetric Catalysis ◽  
Total Syntheses ◽  
Bioactive Natural Products

Total syntheses of polyketide-derived bioactive natural products

2006 ◽  
Vol 6 (4) ◽  
pp. 217-233 ◽  
Author(s):  
Kuniaki Tatsuta ◽  
Seijiro Hosokawa
Keyword(s):  
Natural Products ◽  
Total Syntheses ◽  
Bioactive Natural Products

Total Syntheses of Polyketide-Derived Bioactive Natural Products

ChemInform ◽  
2007 ◽  
Vol 38 (11) ◽  
Author(s):  
Kuniaki Tatsuta ◽  
Seijiro Hosokawa
Keyword(s):  
Natural Products ◽  
Total Syntheses ◽  
Bioactive Natural Products

Total Syntheses of Bioactive Natural Products from Carbohydrates

ChemInform ◽  
2007 ◽  
Vol 38 (12) ◽  
Author(s):  
Kuniaki Tatsuta ◽  
Seijiro Hosokawa
Keyword(s):  
Natural Products ◽  
Total Syntheses ◽  
Bioactive Natural Products

scholarly journals Concise total syntheses of (–)-jorunnamycin A and (–)-jorumycin enabled by asymmetric catalysis

Science ◽  
2018 ◽  
Vol 363 (6424) ◽  
pp. 270-275 ◽  
Author(s):  
Eric R. Welin ◽  
Aurapat Ngamnithiporn ◽  
Max Klatte ◽  
Guillaume Lapointe ◽  
Gerit M. Pototschnig ◽  
...  
Keyword(s):  
Natural Products ◽  
Asymmetric Catalysis ◽  
High Efficiency ◽  
Transition Metal Catalysis ◽  
Metal Catalysis ◽  
Polycyclic Compounds ◽  
Gram Negative ◽  
Total Syntheses ◽  
Bond Forming ◽  
The Past

The bis-tetrahydroisoquinoline (bis-THIQ) natural products have been studied intensively over the past four decades for their exceptionally potent anticancer activity, in addition to strong Gram-positive and Gram-negative antibiotic character. Synthetic strategies toward these complex polycyclic compounds have relied heavily on electrophilic aromatic chemistry, such as the Pictet–Spengler reaction, that mimics their biosynthetic pathways. Herein, we report an approach to two bis-THIQ natural products, jorunnamycin A and jorumycin, that instead harnesses the power of modern transition-metal catalysis for the three major bond-forming events and proceeds with high efficiency (15 and 16 steps, respectively). By breaking from biomimicry, this strategy allows for the preparation of a more diverse set of nonnatural analogs.

Ester coupling reactions – an enduring challenge in the chemical synthesis of bioactive natural products

2015 ◽  
Vol 32 (4) ◽  
pp. 605-632 ◽  
Author(s):  
Michail Tsakos ◽  
Eva S. Schaffert ◽  
Lise L. Clement ◽  
Nikolaj L. Villadsen ◽  
Thomas B. Poulsen
Keyword(s):  
Natural Products ◽  
Chemical Synthesis ◽  
Natural Product ◽  
Organic Synthesis ◽  
State Of The Art ◽  
The State ◽  
Coupling Reactions ◽  
Total Syntheses ◽  
Bioactive Natural Products ◽  
Complex Ester

In this review we investigate the use of complex ester fragment couplings within natural product total syntheses. Using examples from the literature up to 2014 we illustrate the state-of-the-art as well as the challenges within this area of organic synthesis.

Procedure-Economical, Enantioselective Total Syntheses of Polycyclic Natural Products and Analogues Containing a 3a-Hydroxyhexahydropyrrolo[2,3-b]indole-2-carboxylic Acid Residue

Synlett ◽  
2020 ◽  
Vol 31 (17) ◽  
pp. 1681-1690
Author(s):  
Pei-Qiang Huang
Keyword(s):  
Natural Products ◽  
Carboxylic Acid ◽  
Tandem Reactions ◽  
Protecting Group ◽  
Future Perspectives ◽  
Total Syntheses ◽  
Bioactive Natural Products ◽  
Regioselective Reactions ◽  
Enantioselective Syntheses

The 3a-hydroxyhexahydropyrrolo[2,3-b]indole-2-carboxylic acid (HPIC) residue and its aza-analogue are found in many bioactive natural products. In this account, short divergent total syntheses of several such natural products, diastereomers and analogues are described. It is demonstrated that by appropriate combination of different efficient tactics such as biomimetic/bio-inspired synthesis, chemo/regioselective reactions, umpolung of regioselectivity and/or reactivity, and tandem reactions, the enantioselective syntheses of polycyclic molecules such as (+)-asperlicin E and (–)-robustanoids A and B can be achieved in a protecting-group-free and redox-economical manner, in only three to four steps starting from l-tryptophan.1 Introduction2 Strategic Considerations2.1 Occurrence of HO-HPIC and HO-aza-HPIC Residues in Natural Products2.2 Biosyntheses of HO-HPIC and HO-aza-HPIC Residues2.3 Chemical Syntheses of HO-HPIC and HO-aza-HPIC Residues3 Procedure-Economical Syntheses of HO-HPIC-Containing Natural Products3.1 Protecting-Group-Free Syntheses of Asperlicin E, Its Diastereomer, and an Analogue3.2 Divergent Syntheses of (–)-Robustanoids A and B, a Diastereomer, and Analogues4 Conclusion and Future Perspectives

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