Synthesis of the hexacyclic triterpene core of the jujuboside saponins via tandem Wolff rearrangement–intramolecular ketene hetero-Diels–Alder reaction

RR Karimov, DS Tan, DY Gin - Tetrahedron, 2018 - Elsevier
The jujubosides are saponin natural products reported to have immunoadjuvant, anticancer,
antibacterial, antifungal, and antisweet activities. The triterpene component, jujubogenin …

Model studies directed to the synthesis of cucurbitacin IC/D rings

NA Eddy, G Fenteany - Tetrahedron letters, 2015 - Elsevier
Herein, we detail a synthetic strategy toward the C/D rings of cucurbitacin I, a naturally
occurring triterpenoid. This route utilized ring-opening/ring-closing metathesis of a …

Total synthesis of (±)-jujuyane

S Lee, BG Kim, S Geum, J Kim, HY Lee - Organic Letters, 2021 - ACS Publications
The first total synthesis of (±)-jujuyane, a cyclooctanoid natural product, was accomplished
from a (5+ 3) dimerization product of oxidopyrylium ylide that forms the cyclooctanoid core …

Asymmetric de novo synthesis of a cucurbitane triterpenoid: Total synthesis of octanorcucurbitacin B

AR Bucknam, GC Micalizio - Journal of the American Chemical …, 2022 - ACS Publications
The asymmetric de novo synthesis of a cucurbitane natural product, octanorcucurbitacin B,
has been accomplished. Cucurbitanes are a family of structurally complex triterpenoids that …

Synthetic Investigation toward the D‐Ring‐Functionalized Cytotoxic Oleanane‐Type Saponins Pithedulosides D and E

SJ Ge, YH Tu, JH Xia, JS Sun - European Journal of Organic …, 2017 - Wiley Online Library
Leveraging on the orchestrated application of both Schmidt and Yu glycosylations, the first
total syntheses of the echinocystic acid saponins pithedulosides D and E, the two …

Synthesis of the aminocyclopentenediol fragment of queuosine by way of the stereoselective addition of an organometallic reagent to a Nt-butanesulfinyl …

F Heis, E Gallienne, OR Martin - Organic & Biomolecular Chemistry, 2024 - pubs.rsc.org
An innovative, concise synthesis of the aminocyclopentenediol fragment of queuosine is
reported. The synthesis is based on the stereocontrolled addition of a vinylGrignard· LiCl …

Expediently scalable synthesis and antifungal exploration of (+)-yahazunol and related meroterpenoids

S Zhang, X Wang, J Hao, D Li, R Csuk… - Journal of natural …, 2018 - ACS Publications
The efficient synthesis and antifungal exploration of (+)-yahazunol and related natural
products are described. Central to this strategy is the Barton decarboxylative coupling …

Synthesis and cytotoxicity evaluation of d-and l-sugar-containing mono-and bidesmosidic ursane-type saponins

B Sylla, G Jost, S Lavoie, J Legault, C Gauthier… - Bioorganic & Medicinal …, 2024 - Elsevier
Ursolic acid and uvaol are naturally occurring triterpenoids that exhibit a broad spectrum of
pharmacological activities, including cytotoxicity. However, a primary challenge in the …

Bioactive saponins and glycosides. XIV. Structure elucidation and immunological adjuvant activity of novel protojujubogenin type triterpene bisdesmosides …

H Matsuda, T Murakami, A Ikebata… - Chemical and …, 1999 - jstage.jst.go.jp
Following the elucidation of jujubosides A, and C and acetyljujuboside B, novel
protojujubogenin type triterpene bisdesmosides, protojujubosides A, B, and B, were isolated …

Synthesis of sea cucumber saponins with antitumor activities

X Shao, X Wang, K Zhu, Y Dang… - The Journal of Organic …, 2020 - ACS Publications
Holostane glycosides are characteristic metabolites of sea cucumbers, which possess
various biological activities. Here, we report the synthesis of two representative congeners …