Probing the SAR of dEpoB via Chemical Synthesis:  A Total Synthesis Evaluation of C26-(1,3-dioxolanyl)-12,13-desoxyepothilone B

2002 ◽  
Vol 67 (22) ◽  
pp. 7730-7736 ◽  
Author(s):  
Mark D. Chappell ◽  
Christina R. Harris ◽  
Scott D. Kuduk ◽  
Aaron Balog ◽  
Zhicai Wu ◽  
...  
Keyword(s):  
Chemical Synthesis ◽  
Total Synthesis

Computationally Augmented Retrosynthesis: Total Synthesis of Paspaline A and Emindole PB

2018 ◽  
Author(s):  
Timothy Newhouse ◽  
Daria E. Kim ◽  
Joshua E. Zweig
Keyword(s):  
Chemical Synthesis ◽  
Total Synthesis ◽  
Small Molecules ◽  
First Principles ◽  
Quantum Chemical ◽  
Computational Analysis ◽  
Empirical Evaluation ◽  
Synthetic Strategy ◽  
Catalyzed Reactions ◽  
Enzyme Catalyzed Reactions

The diverse molecular architectures of terpene natural products are assembled by exquisite enzyme-catalyzed reactions. Successful recapitulation of these transformations using chemical synthesis is hard to predict from first principles and therefore challenging to execute. A means of evaluating the feasibility of such chemical reactions would greatly enable the development of concise syntheses of complex small molecules. Herein, we report the computational analysis of the energetic favorability of a key bio-inspired transformation, which we use to inform our synthetic strategy. This approach was applied to synthesize two constituents of the historically challenging indole diterpenoid class, resulting in a concise route to (–)-paspaline A in 9 steps from commercially available materials and the first pathway to and structural confirmation of emindole PB in 13 steps. This work highlights how traditional retrosynthetic design can be augmented with quantum chemical calculations to reveal energetically feasible synthetic disconnections, minimizing time-consuming and expensive empirical evaluation.

scholarly journals Linear Triquinane Sesquiterpenoids: Their Isolation, Structures, Biological Activities, and Chemical Synthesis

Molecules ◽  
2018 ◽  
Vol 23 (9) ◽  
pp. 2095 ◽  
Author(s):  
Yi Qiu ◽  
Wen-Jian Lan ◽  
Hou-Jin Li ◽  
Liu-Ping Chen
Keyword(s):  
Chemical Synthesis ◽  
Total Synthesis ◽  
Chemical Structure ◽  
Biological Activities ◽  
Structural Diversity ◽  
Structure Identification ◽  
Important Class ◽  
Soft Corals ◽  
Wide Range ◽  
New Challenges

Linear triquinane sesquiterpenoids represent an important class of natural products. Most of these compounds were isolated from fungi, sponges, and soft corals, and many of them displayed a wide range of biological activities. On account of their structural diversity and complexity, linear triquinane sesquiterpenoids present new challenges for chemical structure identification and total synthesis. 118 linear triquinane sesquiterpenoids were classified into 8 types, named types I–VIII, based on the carbon skeleton and the position of carbon substituents. Their isolation, structure elucidations, biological activities, and chemical synthesis were reviewed. This paper cited 102 articles from 1947 to 2018.

scholarly journals Chemical Synthesis of Rare, Deoxy-Amino Sugars Containing Bacterial Glycoconjugates as Potential Vaccine Candidates

Molecules ◽  
2018 ◽  
Vol 23 (8) ◽  
pp. 1997 ◽  
Author(s):  
Archanamayee Behera ◽  
Suvarn Kulkarni
Keyword(s):  
Chemical Synthesis ◽  
Total Synthesis ◽  
Structural Difference ◽  
Building Blocks ◽  
Host Cells ◽  
Amino Sugars ◽  
Rare Sugar ◽  
Vaccine Candidates ◽  
Potential Vaccine ◽  
Remarkable Progress

Bacteria often contain rare deoxy amino sugars which are absent in the host cells. This structural difference can be harnessed for the development of vaccines. Over the last fifteen years, remarkable progress has been made toward the development of novel and efficient protocols for obtaining the rare sugar building blocks and their stereoselective assembly to construct conjugation ready bacterial glycans. In this review, we discuss the total synthesis of a variety of rare sugar containing bacterial glycoconjugates which are potential vaccine candidates.

The discovery of a freezing-induced peptide ligation during the total chemical synthesis of human interferon-ε

2018 ◽  
Vol 16 (28) ◽  
pp. 5097-5101
Author(s):  
Yin-He Yang ◽  
Bin Di ◽  
Da-Song Yang
Keyword(s):  
Amino Acids ◽  
Chemical Synthesis ◽  
Hiv Infection ◽  
Total Synthesis ◽  
Human Interferon ◽  
Peptide Ligation

The first example of a counterintuitive freezing-induced peptide ligation was discovered during the total synthesis of human interferon-ε (187 amino acids) which blocks HIV infection through unique mechanisms.

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