Article
Chemistry, Organic
Yinxin Liu, Jun Liu, Chuanfang Zhao, Yuguo Du
Summary: The stereoselective total synthesis of siladenoserinols A and D was achieved using carbohydrates as a chiral template. The key feature of this work is the construction of the medicinally privileged 6,8-DOBCO scaffold through a cascade reaction, which could facilitate bioactivity investigation of siladenoserinols.
Article
Chemistry, Organic
Jia-Tian Lu, Yingxiao Zong, Xiaodong Yue, Junke Wang
Summary: The enantioselective synthesis of (+)-isolysergol was achieved in 18 steps with an overall yield of 11% from (2R)-(+)-phenyloxirane. Key steps included a stereoselective intramolecular 1,3-dipolar addition of nitrone with terminal olefin and a Cope elimination to form the D ring. A rhodium-catalyzed intramolecular [3 + 2] annulation of a benzene ring with alpha-imino carbenoid was designed for the late-stage synthesis of the 3,4-fused indole scaffold.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Kuei-Wei Chiu, Yu-Hsun Tseng, Ying-Xin Li, Rong-Jie Chein
Summary: In this study, a novel biomimetic synthesis of clavicipitic acid diastereomers was reported, utilizing a DDQ-mediated crossdehydrogenative coupling (CDC) reaction. The synthesis involved Suzuki coupling for prenylation and an intramolecular CDC reaction for the construction of the azepinoindole core. The trans isomer was obtained as the major product, and the two diastereomers were separable. The CDC reaction conditions were investigated, and a plausible mechanism for diastereoselectivity was proposed.
Article
Chemistry, Multidisciplinary
Baiyang Jiang, Mingji Dai
Summary: This study presents a convergent total synthesis approach for (+/-)-hamigeran M, utilizing five C-H functionalization reactions to achieve the synthesis in 11 steps with an overall yield of 3.9%. Key steps include hydroxy-directed C-H borylation, late-stage oxazole-directed C-H borylation-oxidation, and hydrogen-atom transfer reaction to reduce a challenging tetrasubstituted double bond.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Kenzo Yahata, Raphael J. Zachmann, Alois Fuerstner
Summary: After resolving all the issues surrounding the constitution and stereostructure of prorocentin through a recent total synthesis, a new approach was devised to improve the supply of this scarce marine natural product; this compound is a cometabolite of the phosphatase inhibitor okadaic acid but still lacks detailed biological profiling. The revised method starts from 2-deoxy-D-glucose; the key to success was a telescoped hemiacetal reduction/acetal cleavage and an exquisitely selective gold/Bronsted acid-cocatalyzed spiroacetalization.
Article
Chemistry, Organic
Shan-Shan Li, Li-Li Zhao, Min Pan, Na Feng, Bao-Qiong Li, Xiang-Zhi Zhang, Jin-Bao Peng, Ai-Jun Ma
Summary: An efficient synthesis of (+)-peniciketal B has been achieved in 15 steps from commercially available materials. A concise synthetic approach employing a cascade reaction was used to construct the benzo-fused 2,8-dioxabicyclo[3.3.1]-nonane with excellent stereoselectivity. The generality of the transformation was demonstrated by the broad scope of potential candidates for natural product synthesis and medicinal chemistry.
Article
Chemistry, Multidisciplinary
Baochao Yang, Guang Li, Qian Wang, Jieping Zhu
Summary: An asymmetric synthesis of (+)-stephadiamine has been achieved using a series of reactions, including enantioselective dearomatizative Michael addition, reductive generation of nitrone followed by intramolecular cycloaddition, Curtius rearrangement, benzylic C-H oxidation, and diastereoselective ketone reduction.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Review
Chemistry, Multidisciplinary
Liyan Yang, Zhonglei Wang
Summary: Aflatoxins, produced by various Aspergillus fungi, are natural compounds with pentacyclic structures that pose a risk to human health. Over the past 55 years, there have been significant advancements in the total synthesis of aflatoxins, aiming to better understand their biological activity and presence in food industry samples.
FRONTIERS IN CHEMISTRY
(2021)
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
Takayuki Ohyoshi, Hidetada Iizumi, Shu Hosono, Hikaru Tano, Hideo Kigoshi
Summary: The total synthesis of aplysiasecosterols A and B has been accomplished. Key features of the synthesis include the Suzuki-Miyaura coupling of each AB-ring segment and common D-ring segment. This late-stage convergent synthesis, which has rarely been reported in secosteroid synthesis, can be adapted to many 9,11-secosteroids.
Article
Chemistry, Multidisciplinary
Ya-Jian Hu, Chen-Chen Gu, Xin-Feng Wang, Long Min, Chuang-Chuang Li
Summary: Taxol is a famous natural diterpenoid and important anticancer medicine with synthetic challenges. This study presents an asymmetric total synthesis of Taxol through a concise approach and the efficient construction of the challenging eight-membered ring. The new convergent approach allows for the creation of Taxol derivatives for further biological research.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Peng-Zhen Sheng, Lu-Lu Li, Zhi-Bin Ni, Kun Wei, Yu-Rong Yang
Summary: Cephalotine A, a newly isolated alkaloid from Cephalotaxus, was successfully synthesized enantioselectively via three crucial reactions. These involved SmI2-mediated radical cyclization of lactone and aldehyde for the final ring formation, Chang's iridium-catalyzed C-H amidation for constructing pyrrolidone stereoselectively, and Carreria's dual Ir/amine catalyzed allylation to introduce the neighboring tertiary stereocenters.
Article
Chemistry, Organic
Hongyuan Zhang, Haibing He, Shuanhu Gao
Summary: The asymmetric synthesis of the complex C-18 Cephalotaxus dinorditerpenoid cephanolide B was achieved for the first time using a remote hydroxyl group directed hydrogenation strategy and a sequence of modified transformations. The key hexahydrofluorenone core skeleton and selective reductions were crucial in achieving the target compound.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Peng Zou, Hongjian Yang, Jian Wei, Taimin Wang, Hongbin Zhai
Summary: The first asymmetric total synthesis of three picrinine-type akuammiline alkaloids has been achieved, involving an efficient acid-promoted oxo-bridge ring-opening, an unusual Dauben-Michno oxidation, and a nickel-mediated reductive Heck reaction to forge the [3.3.1]-azabicyclic core.
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)
