Related Experiment Video
Updated: Jul 13, 2026

Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents
Published on: May 28, 2014
Stereochemistry of pladienolide B
Naoki Asai1, Yoshihiko Kotake, Jun Niijima
1Tsukuba Research Laboratories, Eisai Co., Ltd, Tokodai, Tsukuba, Ibaraki, Japan. n2-asai@hhc.eisai.co.jp
Pladienolide B, an antitumor agent from Streptomyces platensis, demonstrates significant potential for cancer treatment. Its precise molecular structure was confirmed using spectral data, paving the way for new drug development.
Area of Science:
- Natural Products Chemistry
- Medicinal Chemistry
- Pharmacology
Background:
- Pladienolide B is a macrolide compound derived from Streptomyces platensis Mer-11107.
- This compound exhibits notable antitumor properties in both laboratory and living organism studies.
- It represents a promising candidate for the development of new anticancer therapies.
Purpose of the Study:
- To investigate the antitumor potential of Pladienolide B.
- To determine the absolute configurations of the ten chiral centers in Pladienolide B.
- To establish Pladienolide B as a lead compound for novel antitumor agents.
Main Methods:
- Isolation of Pladienolide B from Streptomyces platensis Mer-11107.
- Evaluation of in vitro and in vivo antitumor activities.
- Analysis of spectral data (e.g., NMR, Mass Spectrometry) of Pladienolide B and its derivatives.
- Chemical transformations to aid in structural elucidation.
Main Results:
- Pladienolide B demonstrated potent antitumor activity.
- The absolute configurations of ten chiral centers were successfully determined.
- The spectral data provided a comprehensive understanding of Pladienolide B's structure.
Conclusions:
- Pladienolide B is a potent natural product with significant antitumor activity.
- The confirmed stereochemistry is crucial for understanding its mechanism of action and for future drug design.
- Pladienolide B serves as a valuable lead compound for the development of novel anticancer drugs.
More Related Videos
10:21Developing Photosensitizer-Cobaloxime Hybrids for Solar-Driven H2 Production in Aqueous Aerobic Conditions
Published on: October 5, 2019
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Related Concept Videos
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
Thermal Electrocyclic Reactions: Stereochemistry
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
Stereoisomerism
Isomers are different chemical species that have the same chemical formula.
Transition metal complexes often exist as geometric isomers, in which the same atoms are connected through the same types of bonds but with differences in their orientation in space. Coordination complexes with two different ligands in the cis and trans positions from a ligand of interest form isomers. For example, the octahedral [Co(NH3)4Cl2]+ ion has two isomers (Figure 1) In the cis...
Photochemical Electrocyclic Reactions: Stereochemistry
Selection Rules: Photochemical Activation