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Stereocontrolled Synthesis of the Portimine Skeleton via Organocatalyst-Mediated Asymmetric Stannylation and Stereoretentive C()-C() Stille Coupling.
Org Lett
January 2025
Graduate School of Life Sciences, Tohoku University, 2-1-1 Katahira, 980-8577 Aoba-ku, Sendai, Japan.
Our efforts toward the synthesis of the marine natural product portimine are described. The key to the synthesis of the skeleton is a stereoretentive copper-catalyzed C()-C() Stille-type cross-coupling that enables the convergent assembly of functionalized fragments. The core skeleton of portimine was constructed via ring-closing metathesis and transannular acetal formation.
View Article and Find Full Text PDFTotal synthesis of linear lipodepsipeptide kavaratamide A and its C25-epimer.
Org Biomol Chem
January 2025
Organic Chemistry Division, CSIR-National Chemical Laboratory, Dr Homi Bhabha Road, Pune-411008, India.
We report the stereoselective total synthesis of kavaratamide A, a linear lipodepsipeptide from the cyanobacterium (collected in Kavaratti, India), and its unnatural C25-epimer. The convergent approach employs Keck asymmetric allylation to construct the chiral β-hydroxy carboxylic acid fragment [(3)-HDA; 3-hydroxydecanoic acid], while the peptide unit was assembled from L-Val, -Me-L-Ala, ()-Hiva, and ()-Pr--Me-pyr using well-orchestrated coupling methods to prevent racemization. Modifications to the Keck allylation conditions enabled the synthesis of the C25-epimer with good yield.
View Article and Find Full Text PDFCatalytic Asymmetric Total Synthesis of (+)-Chamaecydin and (+)-Isochamaecydin and their Stereoisomers.
Angew Chem Int Ed Engl
January 2025
Jilin Province Key Lab of Green Chemistry and Process, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, 5625 Renmin Street, Changchun, Jilin, 130022, China.
A modular approach was developed for the first catalytic asymmetric total syntheses of naturally occurring C terpene quinone methides and their non-natural stereoisomers, which feature the presence of an unprecedented spiro[4.4]nonane-containing 6-6-6-5-5-3 hexacyclic skeleton. Resting on a chiral phosphinamide-catalyzed enantioselective reduction of 2,2-disubstituted cyclohexane-1,3-dione, a concise route for the synthesis of enantioenriched 6-6 bicyclic fragment was developed.
View Article and Find Full Text PDFConvergent Total Synthesis of Ixabepilone and Its Analogues Enabled by Highly Efficient Asymmetric Hydrogenations.
Chemistry
December 2024
Chemistry and Chemical Engineering Guangdong Laboratory, Shantou, China.
The convergent total synthesis of ixabepilone and its analogues in a 13-step longest linear sequence is reported. The crucial chiral centers at challenging C3-O, C8-C and C15-N positions on the scaffold of the ixabepilone were installed via highly efficient asymmetric hydrogenations (up to 95 % yield and up to 99 % e.e.
View Article and Find Full Text PDFInformation propagation dynamics on heterogeneous-homogeneous coupling bi-layer networks.
Sci Rep
December 2024
State Key Laboratory of Media Convergence and Communication, Communication University of China, Beijing, 100024, China.
The proliferation of multi-platform network information has expanded communication channels for users, enabling the integration and dissemination of information across both Social Networking Services (SNS)-type app and Instant Message (IM)-type app. With the intensification of convergent communication, some users in the two types of apps show active alternation in spreading information to each other's platforms. The study of the evolution trend of information in different platforms is of great practical significance for the mastery of the communication law.
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