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
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)
Review
Biochemistry & Molecular Biology
Jian Yang, Demeng Xie, Xiaofeng Ma
Summary: Amino sugars, carbohydrates with hydroxyl groups replaced by an amino group, play crucial roles in various biological activities. Stereoselective glycosylation of amino sugars has been a continuous effort, but it is challenging due to the competitive coordination of the amine to the Lewis acid promoter. This review focuses on the updated overview of stereoselective synthesis of 1,2-cis-aminoglycoside and its applications in complex glycoconjugate synthesis.
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, 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, Multidisciplinary
Kevin George, Pavithra Elavarasan, Shanmugam Ponnusamy, Kannadasan Sathananthan
Summary: A facile and efficient method for the synthesis of quinoline-fused fluorescent dihydro/spiroquinazolinones has been developed, with successful synthesis of various compounds and testing of the photoelectric properties of two specific derivatives.
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, Organic
Fabia Mittendorf, Ibrahim-Ethem Celik, Stefan F. Kirsch
Summary: This study reports the modular synthesis of 1,3-polyols using a chiral phosphine oxide building block. The versatile building block can be repetitively used for stereocontrolled synthesis of a tetraol key intermediate, allowing for the total synthesis of the potentially anti-inflammatory natural product cryptoconcatone D. A new route towards the chiral building block starting from 2-deoxy-D-ribose is also presented, making the use of the building block more attractive.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Mariya Novakova, Anupama Das, Catherine Alex, Alexei V. V. Demchenko
Summary: This study presents a streamlined synthesis of a rare sugar D-altrosamine and investigates the glycosylation of different glycosyl acceptors using differentially protected altrosamine donors. High facial stereoselectivity is achieved through the H-bond-mediated aglycone delivery (HAD) pathway with 3-O-picoloyl donors and reactive glycosyl acceptors. In contrast, glycosidations with altrosamine donors equipped with the 3-O-benzoyl group show poor stereoselectivity.
FRONTIERS IN CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Emma Naulin, Marine Lombard, Vincent Gandon, Pascal Retailleau, Elsa Van Elslande, Luc Neuville, Geraldine Masson
Summary: This study reports a method for selectively controlling the regioselectivity of conjugated trienes and synthesizing chiral cis-3,6-dihydro-2H-1,2-oxazines. Modular access to three different regioisomers is achieved, and the utility of each regioisomeric cycloadduct is highlighted.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Review
Chemistry, Organic
Regina Westphal, Eclair Venturini Filho, Fabrizio Medici, Maurizio Benaglia, Sandro J. Greco
Summary: This review summarizes the latest developments in asymmetric domino reactions, with a focus on the preparation of spiro compounds. Discussions on the stereoselectivity of the transformations, reaction mechanisms, rationalization of the stereochemical outcome, and the applications of domino reactions to the synthesis of biologically active molecules and natural products are included.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Organic
Limin Wang, Longhui Duan, Biqiong Hong, Zhenhua Gu
Summary: An acid-mediated electrophilic cyclization of 2-alkynyl-1,1'-biphenyls was used to synthesize angular, bent, and zigzag fused nonplanar conjugated organic molecules. The reaction involved a Wagner-Meerwein-type rearrangement via a spiro carbocation intermediate formed by electrophilic cyclization of a 9H-fluoren-9-one derivative. The resulting products could be further transformed into helical fluorenes with high fluorescence quantum yields.
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)
