scholarly journals On the Structure of (R)-2-Methylheptyl Isonicotinate: Evidence for the Structural Solution from Total Synthesis

2018 ◽  
Vol 13 (3) ◽  
pp. 1934578X1801300
Author(s):  
Mangala Gowri Ponnapalli ◽  
Narayana Rao Gundoju ◽  
Harikiran Theerthala ◽  
Ramesh Bokam ◽  
Nageswara Rao Yalavarthi
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Molecular Identification ◽  
Total Syntheses ◽  
Ethylhexyl Phthalate ◽  
Microbial Agent ◽  
Structural Solution

The controversial molecular identification of ( R)-2-methylheptyl isonicotinate (1) has been settled. Despite its significance as a potent anti-microbial agent against several clinically relevant pathogens, the structure of natural product is uncertain so far due to controversial reports. Its structure has been resolved as bis (2-ethylhexyl) phthalate (2) by total syntheses of chain isomers. In addition, we have also revised bis (2-methylheptyl) phthalate (3) as (2) in some reports.

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.

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 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.

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 A Concise Total Synthesis of the Fungal Isoquinoline Alkaloid TMC-120B

Molecules ◽  
2022 ◽  
Vol 27 (2) ◽  
pp. 521
Author(s):  
Ahmad K. Haidar ◽  
Niels D. Kjeldsen ◽  
Nikolaj S. Troelsen ◽  
Viola Previtali ◽  
Kasper P. Lundquist ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Isoquinoline Alkaloid ◽  
Total Syntheses ◽  
Antiepileptic Activity ◽  
Short Synthesis

Recent reports of antiepileptic activity of the fungal alkaloid TMC-120B have renewed the interest in this natural product. Previous total syntheses of TMC-120B comprise many steps and have low overall yields (11–17 steps, 1.5–2.9% yield). Thus, to access this compound more efficiently, we herein present a concise and significantly improved total synthesis of the natural product. Our short synthesis relies on two key cyclization steps to assemble the central scaffold: isoquinoline formation via an ethynyl-imino cyclization and an intramolecular Friedel-Crafts reaction to form the furanone.

Total Synthesis of Natural Products Using Intramolecular Nozaki–Hiyama–Takai–Kishi Reactions

Synlett ◽  
2020 ◽  
Vol 31 (05) ◽  
pp. 421-433 ◽  
Author(s):  
Ken-ichi Takao ◽  
Akihiro Ogura ◽  
Keisuke Yoshida ◽  
Siro Simizu
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
Natural Product Synthesis ◽  
Total Syntheses

In this Account, we describe our studies on the total synthesis of several natural products using intramolecular Nozaki–Hiyama–Takai–Kishi (NHTK) reactions. In each synthesis, an NHTK reaction is used to efficiently construct a medium-sized ring. These examples demonstrate the utility of the intramolecular NHTK reaction in natural product synthesis.1 Introduction2 Total Synthesis of (+)-Pestalotiopsin A3 Total Synthesis of (+)-Cytosporolide A4 Total Synthesis of (+)-Vibsanin A5 Total Syntheses of (+)-Aquatolide and Related Humulanolides6 Conclusion

Nonbiomimetic total synthesis of indole alkaloids using alkyne-based strategies

2021 ◽  
Vol 19 (16) ◽  
pp. 3551-3568
Author(s):  
Hiroaki Ohno ◽  
Shinsuke Inuki
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Indole Alkaloids ◽  
Natural Product Synthesis ◽  
Total Syntheses

Significance of nonbiomimetic natural product synthesis and nonbiomimetic total syntheses of indole alkaloids based on the construction of core structures using alkyne reactions are summarized in this review.

scholarly journals 4-Step Total Synthesis of (−)-Pavidolide B

2020 ◽  
Author(s):  
Yaoqiu Zhu ◽  
Elkin L. Romero ◽  
Kolluru Srinivas ◽  
Elizabeth Noriega
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Michael Addition ◽  
Cascade Reaction ◽  
Asymmetric Total Synthesis ◽  
Total Syntheses ◽  
One Step

(−)-Pavidolide B is a complex tetracyclic diterpenoid with seven contiguous stereocenters, and classical total syntheses have recently been reported. In this work, an annulation strategy of carbanion cascade reaction is formulated for accomplishing an asymmetric total synthesis of (−)-pavidolide B in just 4 linear steps. The key reaction is a tandem intramolecular Michael addition, which constructs two 5-membered rings and five stereocenters in a highly selective fashion in one step. This work represents one of the most efficient cases of total synthesis and demonstrates that synthetic access to complex therapeutic natural product can be greatly simplified.

scholarly journals 4-Step Total Synthesis of (−)-Pavidolide B

2020 ◽  
Author(s):  
Yaoqiu Zhu ◽  
Elkin L. Romero ◽  
Kolluru Srinivas ◽  
Elizabeth Noriega
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Michael Addition ◽  
Cascade Reaction ◽  
Asymmetric Total Synthesis ◽  
Total Syntheses ◽  
One Step

(−)-Pavidolide B is a complex tetracyclic diterpenoid with seven contiguous stereocenters, and classical total syntheses have recently been reported. In this work, an annulation strategy of carbanion cascade reaction is formulated for accomplishing an asymmetric total synthesis of (−)-pavidolide B in just 4 linear steps. The key reaction is a tandem intramolecular Michael addition, which constructs two 5-membered rings and five stereocenters in a highly selective fashion in one step. This work represents one of the most efficient cases of total synthesis and demonstrates that synthetic access to complex therapeutic natural product can be greatly simplified.

Isolation, Synthesis, and Biological Activity of Quindoline, a Valuable­ Indoloquinoline Natural Product and Useful Key Intermediate­

Synthesis ◽  
2018 ◽  
Vol 50 (07) ◽  
pp. 1417-1429 ◽  
Author(s):  
Teodoro Kaufman ◽  
María Méndez ◽  
Andrea Bracca
Keyword(s):  
Biological Activity ◽  
Total Synthesis ◽  
Natural Product ◽  
Natural Source ◽  
Total Syntheses ◽  
Naturally Occurring ◽  
The World ◽  
Biological Tests ◽  
Synthetic Studies

Quindoline is one of the simplest naturally occurring monomeric indoloquinoline alkaloids. Chemists exhibited interest in this compound before it was isolated from a natural source. The different approaches toward the total synthesis of the natural product and its performance in various biological tests are discussed. Aspects related to the isolation of quindoline from different ethnomedicinally relevant plants around the world are also reviewed.1 Introduction2 Isolation and Biogenetic Considerations3 Total Syntheses of Quindoline3.1 Early Synthetic Studies3.2 Syntheses from Benzenoids3.3 Syntheses from Indoles3.4 Syntheses from Quinolines4 Biological Activity Studies5 Conclusions

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