Article
Chemistry, Organic
Foqing Ma, Chenxi He, Eryu Wang, Rongbiao Tong
Summary: A new collective synthetic strategy is reported in this study, featuring a green chemistry approach for constructing the common cis-fused DHQ core. The collective total syntheses of lepadins A-E and H are accomplished from the common DHQ core within 10 steps.
Article
Chemistry, Organic
Chao Wang, Dong Pei, Li Zhou, Jian Sun
Summary: Practical methods for the synthesis of three stereoisomers of Entecavir have been developed using the reported intermediates (1S,2R)-2-((benzyloxy)methyl)cyclopent-3-en-1-ol and (1R,2S)-2-((benzyloxy)methyl)cyclopent-3-en-1-ol. The overall yields of the three stereoisomers are 17-20%. Other stereoisomers could also potentially be synthesized using the materials and reactions described in this article.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Organic
Eilidh G. Young, Phillip S. Grant, Daniel P. Furkert, Margaret A. Brimble
Summary: Lycibarbarines A-C are spirocyclic alkaloids with a unique tetracyclic framework. The first total syntheses of lycibarbarines A-C were achieved over 10 steps. The spiroketal unit of lycibarbarines A-C exhibits unusually high resistance to acid-mediated isomerization and epimerization.
Article
Chemistry, Organic
Dhiman Saha, Gour Hari Mandal, Rajib Kumar Goswami
Summary: A convergent route has been developed for the asymmetric total synthesis of potent anticancer polyketide natural product amphirionin-2, with key features including Sharpless asymmetric dihydroxylation, cycloetherification, Wittig olefination, Julia-Kocienski olefination, and Crimmins propionate aldol reaction after the proposed structures of amphirionin-2 were revised based on a recent report.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Runze Mao, Daniel J. J. Wackelin, Cooper S. S. Jamieson, Torben Rogge, Shilong Gao, Anuvab Das, Doris Mia Taylor, K. N. Houk, Frances H. H. Arnold
Summary: By engineering bacterial cytochrome P450, chiral 1,2,3-polysubstituted cyclopropanes can be synthesized regardless of the stereopurity of the olefin substrates used. This new method simplifies the synthesis of chiral cyclopropanes and expands the application of classical cyclopropanation methods.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Yuan Jin, Kensuke Orihara, Fumiki Kawagishi, Tatsuya Toma, Tohru Fukuyama, Satoshi Yokoshima
Summary: The total synthesis of Haliclonin A was achieved through a series of reactions including Birch reduction/alkylation, ring-closing metathesis, intramolecular cyclopropanation, and stereoselective 1,4-addition, leading to the formation of the desired compound.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Moinul Haque Sahana, Dhiman Saha, Rajib Kumar Goswami
Summary: The stereoselective total synthesis of structurally intriguing anti-malarial macrolide strasseriolide A has been successfully achieved by adopting a convergent approach. This approach involves several reactions such as selective reduction, aldol reaction, alkylation, olefination, macrolactonization, and selective saponification. It was also found that the 13C{1H} NMR data of strasseriolide A are highly sensitive to its solution concentration.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Yue Hu, He Gu, Yuanliang Jia, Guiyin Luo, Xiaochuan Chen
Summary: A flexible approach to both type II and III lepadin alkaloids is developed for the first time. It involves employing a novel chiral ketolactone dienophile and an intramolecular nucleophilic amination to synthesize lepadin frameworks with different stereochemical types.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Organic
Liselle Atkin, Angus Robertson, Jonathan M. White, Mark A. Rizzacasa
Summary: The total synthesis of viridiofungins A and B via beta-lactone 3 in 13 steps is described, with key steps including an HF-mediated rearrangement, olefin cross metathesis while suppressing isomerization, and a novel beta-lactone ring opening. Deprotection yielded either viridiofungin A or B in high yield.
Article
Chemistry, Multidisciplinary
Daniele Fiorito, Selbi Keskin, Joseph M. Bateman, Malcolm George, Adam Noble, Varinder K. Aggarwal
Summary: This study presents a strategy for the stereocontrolled synthesis of 1,5-polyols using enantiopure magnesium carbenoids. By merging boronic ester homologation and transition-metal-catalyzed alkene hydroboration and diboration, the acyclic backbone of bastimolide B was rapidly assembled with full control over the remote stereocenters.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Yuta Miyamoto, Arihiro Iwasaki, Haruka Fujimura, Chihiro Kudo, Naoaki Kurisawa, Osamu Ohno, Kiyotake Suenaga
Summary: Caldorazole, a novel polyketide, was isolated from a marine cyanobacterium in 2022. Despite lacking chiral centers, it exhibits potent inhibitory activity against mitochondrial respiratory chain complex I. To study its structure-activity relationship, we accomplished the first total synthesis of caldorazole using a convergent synthetic route, aiming to establish a method for obtaining caldorazole without relying on biological resources.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Moinul Haque Sahana, Debobrata Paul, Himangshu Sharma, Rajib Kumar Goswami
Summary: A convergent route for the asymmetric total synthesis of antibacterial macrolide sorangiolide A has been developed, incorporating key reactions to address the low intensity of C1 and C2 center NMR signals and revealing the possible forms of existence for the natural product in solution.
Article
Chemistry, Multidisciplinary
Gleb A. Chesnokov, Karl Gademann
Summary: The marine-derived compound Peyssonnoside A was successfully synthesized for the first time in a concise, efficient, scalable, and highly diastereoselective manner. The aglucone peyssonnosol was achieved in 21% overall yield after 15 steps, with key reactions including Simmons-Smith cyclopropanation and Mukaiyama hydration controlled by the spatial structure of the substrates.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
He Gu, Yue Hu, Yuanliang Jia, Qin Zhou, Guiyin Luo, Xiaochuan Chen
Summary: An efficient approach to synthesize type III lepadin alkaloids (lepadins F and G) was developed through a key Diels-Alder reaction using a novel ketolactone-type dienophile with a chiral diol unit to achieve excellent regio- and stereoselectivity control for the desired all-cis-trisubstituted cyclohexene. Subsequent selective sulfonylation of the diol unit followed by S(N)2 cyclization under hydrogenation conditions successfully constructed the substituted piperidine ring.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Fanglin Xue, Hengmao Liu, Rui Wang, Dan Zhang, Hao Song, Xiao-Yu Liu, Yong Qin
Summary: A catalytic asymmetric total synthesis of (+)-vincamine is reported, featuring a Pd-catalyzed enantioselective decarboxylative allylation and a stereoselective iminium reduction.
CHINESE CHEMICAL LETTERS
(2022)
