Article
Chemistry, Multidisciplinary
Jihui Gao, Chuan He
Summary: Silanols are valuable compounds with applications in materials science, synthetic chemistry, and medicinal chemistry. Despite some developed approaches for synthesizing various silanols, the access to enantioenriched silicon-stereogenic silanols remains limited. This Concept article summarizes recent advances in constructing silicon-stereogenic silanols and encourages further research in this area.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Review
Chemistry, Multidisciplinary
Guang-Jian Mei, Wai Lean Koay, Chuan Xiang Alvin Tan, Yixin Lu
Summary: Pyrroloindolines are important polycyclic indoline motifs widely found in natural products and bio-significant molecules, presenting a challenge to organic chemists with their rigid tricyclic molecular architectures and fully substituted carbon center at the C3a-position. Alkaloids containing pyrroloindoline display promising activities, making them significant in biological sciences and drug development. In recent decades, the synthetic targets of pyrroloindoline and analogues have attracted tremendous attention from the synthetic community, with a focus on catalytic asymmetric synthesis and total synthesis applications.
CHEMICAL SOCIETY REVIEWS
(2021)
Review
Biochemistry & Molecular Biology
Rebekah G. Reynolds, Huong Quynh Anh Nguyen, Jordan C. T. Reddel, Regan J. Thomson
Summary: This review provides a comprehensive overview of the diverse strategies employed by chemists for achieving enantioselective total syntheses of cyclolignans from 2000 to 2021. These natural products, with biological properties such as anti-inflammatory and antiviral activities, have been popular synthetic targets due to their structural diversity and utility in medicine.
NATURAL PRODUCT REPORTS
(2022)
Review
Chemistry, Multidisciplinary
Long Min, Jing-Chun Han, Wen Zhang, Chen-Chen Gu, Yun-Peng Zou, Chuang-Chuang Li
Summary: This article reviews the progress made in the total synthesis of Taxol in the last few decades, including the development of synthetic strategies and key lessons learned. It also briefly discusses the future of research in this area.
Review
Chemistry, Organic
Andre R. Paquette, Christopher N. Boddy
Summary: This review analyzes three strategies for the total synthesis of cyclic depsipeptide natural products, and introduces selective synthesis methods and application fields of different strategies.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Phil C. Knutson, Haofan Ji, Christopher M. Harrington, Yan-Ting Ke, Eric M. Ferreira
Summary: This study describes two strategies for enantioselective total synthesis of gelsenicine. One approach using chirality transfer cyclization fell short, while a separate asymmetric catalysis route utilizing bisphosphine-gold-catalyzed cyclization was pursued. A catalytic system was identified that provided a synthetic intermediate in high enantiopurity, allowing for the enantioselective formal total synthesis of (+)-gelsenicine.
Review
Biochemistry & Molecular Biology
Zhixian Ma, Ankun Zhou, Chengfeng Xia
Summary: This review summarizes the structural diversity and chemical synthesis of complex cyclotryptamine alkaloids with a bispyrrolidino[2,3-b]indoline (BPI) skeleton. These compounds exhibit wide systematic occurrences, large structural diversity, and multiple biological activities. Despite their structural complexity, remarkable progress has been made in the last six decades, and several successful methods have been established for their construction.
NATURAL PRODUCT REPORTS
(2022)
Review
Chemistry, Multidisciplinary
Alois Fuerstner
Summary: Macrocyclic natural products are abundant in various domains of life, providing significant advantages to producing organisms. While macrocyclization reactions were traditionally perceived as challenging, recent methodological advances have greatly alleviated this difficulty, allowing for more systematic exploration of the benefits provided by large and medium-size ring systems. Moreover, the increasing understanding of conformational peculiarities in large rings and the development of new catalytic reactions have opened up opportunities for rapid increases in molecular complexity.
ACCOUNTS OF CHEMICAL RESEARCH
(2021)
Review
Chemistry, Multidisciplinary
Lu Liu, Minghua Jiang, Qingkang Zhang, Hong Chen, Yifu Zhang, Jian Zhang
Summary: This paper summarizes the asymmetric synthesis strategies of halichlorine and pinnaic acid, two structurally related natural alkaloids with diverse biological effects. The unique structure and potential biological activity of these compounds have attracted significant synthetic interest, making them a research focus in recent years. The review provides guidance for related work by highlighting the use of a 6-azaspiro[4.5]decane skeleton as a key intermediate in the synthesis strategies.
Article
Chemistry, Organic
Zhi Zhang, Yunfeng Li, Rentao Zhang, Xiaoming Yu
Summary: The total synthesis of geldanamycin, a well-known polyketide with potent anticancer activity, was completed in 26 linear steps with an overall yield of 2.65%. High convergency was achieved by disconnecting between C12 and C13 to create C5-C12 and C13-C21 fragments, and using an alkynyl ketone as the precursor for the CS-C12 fragment allowed for reagent-controlled establishment of C7 chirality and flexible substituent exchange at C8.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Kosuke Ohsawa, Sakiko Fukaya, Takayuki Doi
Summary: The structure of the 30-membered cyclodepsipeptide decatransin was determined through total synthesis. Two enantiomers of 2-hydroxy-5-methylhexanoic acid derivatives were prepared and N-alkyl-enriched peptide fragments were synthesized using the Cbz strategy. The synthesis of putative candidates was achieved through convergent peptide coupling and macrocyclization under the Mitsunobu conditions.
Review
Nanoscience & Nanotechnology
Theodore Hueckel, Glen M. Hocky, Stefano Sacanna
Summary: Atoms serve as an inspiration for colloidal self-assembly, allowing building blocks to combine and confer functionality through principles like directionality, valence, and reversible binding. Tetrahedral structures inspired by carbon atoms bonding are now accessible through molecular mimetic colloidal building blocks. Complex colloidal particles can be synthesized and arranged in their own periodic table, leading to diverse assembly routes based on unique particle shape and surface chemistry.
NATURE REVIEWS MATERIALS
(2021)
Review
Chemistry, Multidisciplinary
Jonathan H. George
Summary: Natural products are biosynthesized using a limited pool of starting materials, while biomimetic total synthesis attempts to replicate predisposed pathways using chemical reagents. By avoiding the use of protecting groups, researchers aim to explore the innate reactivity of biosynthetic intermediates. Biomimetic synthesis is often concise and efficient, following atom, step, and redox economies of synthesis.
ACCOUNTS OF CHEMICAL RESEARCH
(2021)
Review
Immunology
Jingyun Wang, Keying Liang, Li Chen, Xiaoling Su, Daoyong Liao, Jianwei Yu, Jun He
Summary: Mycoplasmas, the smallest self-replicating organisms, are capable of causing infections in humans and animals. They have developed various evasion strategies to avoid immune responses, including invasion, biofilm formation, and modulation of immune reactions.
FRONTIERS IN CELLULAR AND INFECTION MICROBIOLOGY
(2023)
Article
Chemistry, Organic
Haofan Ji, Phil C. Knutson, Christopher M. Harrington, Yan-Ting Ke, Eric M. Ferreira
Summary: This article describes a comprehensive and enantioselective total synthesis of (+)-gelsenicine. Two different strategies based on catalytic cycloisomerization as the central step are proposed. One strategy involves chirality transfer from enantioenriched substrates, while the other employs asymmetric catalysis. The chirality transfer strategy is less effective, whereas the latter strategy utilizes phosphoramidite- and bisphosphine-gold complexes to provide a high enantiopurity key intermediate in the Gelsemium alkaloid syntheses. (c) 2023 Elsevier Ltd. All rights reserved.
Article
Chemistry, Multidisciplinary
Hugh Nakamura, Kosuke Yasui, Yuzuru Kanda, Phil S. Baran
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2019)
Article
Chemistry, Multidisciplinary
Yuzuru Kanda, Hugh Nakamura, Shigenobu Umemiya, Ravi Kumar Puthukanoori, Venkata Ramana Murthy Appala, Gopi Krishna Gaddamanugu, Bheema Rao Paraselli, Phil S. Baran
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2020)
Article
Chemistry, Multidisciplinary
Gen Li, Yuzuru Kanda, Seung Youn Hong, Alexander T. Radosevich
Summary: An organophosphorus-catalyzed C-N bond-forming reductive coupling of nitroalkanes with arylboronic acids and esters has been reported. The method exhibits excellent chemoselectivity for the nitro/boronic acid substrate pair, facilitating the synthesis of functionally-rich N-(hetero)arylamines. The identification of a sterically reduced phosphetane catalyst enables the productive coupling in the P(III)/P(V)=O redox manifold, by affecting post-rate-limiting steps and avoiding deleterious side-paths.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)