Article
Chemistry, Multidisciplinary
Si-Hua Hou, Adriana Y. Prichina, Guangbin Dong
Summary: The development of a deconstructive strategy for the first asymmetric synthesis of (-)-thebainone A was described, utilizing an enantioselective C-C bond activation and a C-O bond cleavage reaction. The newly optimized conditions show broad substrate scope and excellent enantioselectivity (up to 99.5:0.5 er). The synthesis of (-)-thebainone A was completed by taking advantage of boron-mediated ether bond cleavage through two complementary routes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Marko Nesic, David B. Ryffel, Jonathan Maturano, Michael Shevlin, Scott R. Pollack, Donald R. Gauthier Jr, Pablo Trigo-Mourin, Li-Kang Zhang, Danielle M. Schultz, Jamie M. McCabe Dunn, Louis-Charles Campeau, Niki R. Patel, David A. Petrone, David Sarlah
Summary: The collaborative total synthesis of darobactin A, a selective antibiotic against Gram-negative bacteria, has been achieved in a convergent manner using D-Garner's aldehyde and L-serine as starting materials. The synthesis involved 16 steps and three scalable routes were developed to synthesize non-canonical amino acids. The closure of the bismacrocycle was successfully achieved through sequential, halogen-selective Larock indole syntheses, with the cyclization order playing a crucial role in the formation of the desired atropisomer.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Yuichiro Kawamoto, Hideki Kitsukawa, Toyoharu Kobayashi, Hisanaka Ito
Summary: The enantioselective total synthesis of nesteretal A was accomplished in 15 steps through biomimetic cascade hemiacetalizations, along with other key features like Sharpless asymmetric dihydroxylation, diastereoselective 1,2-addition, Pd-catalyzed ene-type cyclization, and stereoselective epoxidation to construct a complex structure containing multiple quaternary carbons.
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.
Article
Chemistry, Multidisciplinary
K. C. Nicolaou, Saiyong Pan, Yogesh Shelke, Dipendu Das, Qiuji Ye, Yong Lu, Susanta Sau, Ruiyang Bao, Stephan Rigol
Summary: A new strategy for the total synthesis of Halichondrin B was described in this study, presenting a novel approach that allows for improved syntheses of complex compounds. The method involves the reversal of sequential construction and the coupling of defined fragments to achieve a convergent pathway.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Vasil H. Vasilev, Lukas Spessert, Kuan Yu, Thomas J. Maimone
Summary: The large family of daphnane diterpene orthoesters (DDOs) represents a remarkable class of natural products both in terms of structure and function. They are potent lead compounds for the treatment of pain, neurodegeneration, HIV/AIDS, and cancer. However, the synthesis of DDO natural products remains rare.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Jyoti Shukla, Manoj Kumar Gangwar, Dipankar Koley
Summary: The total synthesis of (-)-delta-lycorane is achieved through organocatalytic Mannich reaction and diastereoselective conjugate addition. Various reactions including Bischler-Napieralski reaction and ring closing metathesis are utilized.
NEW JOURNAL OF CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Long Min, Li-Ping Zhong, Chuang-Chuang Li
Summary: Steroids continue to play a significant role in organic chemistry, medicinal chemistry, and drug discovery. However, the synthesis of unusual rearranged steroids, particularly abeo-steroids with a medium-sized ring, remains a challenge. This Account summarizes the laboratory's efforts in the total synthesis of abeo-steroids using cycloaddition strategies, highlighting the efficiency and versatility of each strategy in constructing structurally complex abeo-steroid cores. The findings provide valuable insights for advancing the total synthesis of abeo- and related steroids.
ACCOUNTS OF CHEMICAL RESEARCH
(2023)
Article
Chemistry, Multidisciplinary
Zhuang Chen, Kuan Zhao, Yanxing Jia
Summary: This study presents a bioinspired total synthesis of (+)-euphorikanin A, which features a fascinating and intricate tetracyclic skeleton with a bridged [3.2.1]-gamma-lactone moiety. Key transformations involve stereoselective alkylation and aldol condensation to introduce the main stereocenters, an intramolecular nucleophile-catalyzed aldol lactonization of carboxylic acid-ketone to form the five-membered ring, a McMurry coupling to construct the seven-membered ring, and a biomimetic benzilic acid type rearrangement to generate the bridged [3.2.1]-gamma-lactone moiety.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Shota Iiyama, Keisuke Fukaya, Yu Yamaguchi, Ami Watanabe, Hiroaki Yamamoto, Shota Mochizuki, Ryosuke Saio, Takashi Noguchi, Takeshi Oishi, Takaaki Sato, Noritaka Chida
Summary: The total synthesis of paclitaxel is achieved through a double Rubottom oxidation of the bis(silyl enol ether) derived from a tricarbocyclic diketone, efficiently installing a bridgehead olefin and C-5/C-13 hydroxy groups in one step. Additionally, a novel Ag-promoted oxetane formation method is used to smoothly construct the tetracyclic framework of paclitaxel.
Article
Chemistry, Organic
Shengzhen Deng, Hongjin Xu, Huanfeng Jiang, Zhiqiang Ma
Summary: An efficient and enantioselective synthesis of an architecturally unusual ergostane-type steroid, dankasterone B, is described. The cis-decalin skeleton of the steroid is established through an intramolecular metal-catalyzed hydrogen atom transfer (MHAT) reaction, while the 13(14 -> 8)abeo-ergostane skeleton is constructed via a radical rearrangement.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Mengmeng Xu, Min Hou, Haibing He, Shuanhu Gao
Summary: This study developed a new synthetic method for constructing aryltetralin lactone lignans and successfully synthesized several natural lignans using this methodology. The synthesized aglacins and small-molecule library created new opportunities for SAR studies of the podophyllotoxin family of natural products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Xianhuang Zeng, Dale L. Boger
Summary: The total synthesis of (-)-strempeliopine involves a powerful SmI2-mediated and BF3 center dot OEt2-initiated dearomative transannular radical cyclization onto an indole, resulting in the formation of a quaternary center and the strategic C19-C2 bond in its core structure.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Fangzhi Han, Guangju Liu, Xuhai Zhang, Yahui Ding, Liang Wang, Yijing Wu, Yue Chen, Quan Zhang
Summary: For the first time, the 15-membered cyclic depsipeptide boholamide A and an epimer were prepared by total synthesis, leading to a revision of the C6 stereochemistry in the original proposed structure. The revised boholamide A was synthesized in 16 linear steps with an overall yield of 5.46%, facilitating investigations into its potential as a hypoxia-selective anticancer agent.
Article
Chemistry, Multidisciplinary
Yang Wang, Yongjian Su, Yanxing Jia
Summary: In this research, the structurally intriguing diterpene (+)-aberrarone was synthesized in only 12 steps from commercially available (S,S)-carveol without protecting group manipulations. This concise synthesis includes a Cu-catalyzed asymmetric hydroboration to generate the chiral methyl group, a Ni-catalyzed reductive coupling to link two fragments, and a Mn-mediated radical cascade cyclization to construct the triquinane system.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
