Related Experiment Video
Updated: Jun 9, 2026
11:04
Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
A concise total synthesis of amphidinolide T2
Huoming Li1, Jinlong Wu, Jialu Luo
1Laboratory of Asymmetric Catalysis and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, PR China.
Chemistry (Weinheim an Der Bergstrasse, Germany)
|August 31, 2010
Summary
Ring-closing metathesis and asymmetric dihydroxylation were used to synthesize amphidinolide T2. This 16-step process yielded the crucial 12,13-diol intermediate for the total synthesis.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Natural Product Synthesis
Background:
- Amphidinolide T2 is a complex marine macrolide with potential biological activity.
- Efficient synthetic routes are crucial for accessing such complex molecules for further study.
Purpose of the Study:
- To develop a regioselective synthetic route towards amphidinolide T2.
- To establish a key intermediate for the total synthesis of amphidinolide T2.
Main Methods:
- Regioselective ring-closing metathesis (RCM) to form an endocyclic double bond.
- Osmium-catalyzed asymmetric dihydroxylation (AD) of the double bond.
- A 16-step linear synthesis strategy.
Main Results:
- The synthesis successfully formed the (12E)-endocyclic double bond via RCM.
- Asymmetric dihydroxylation yielded the required 12,13-diol intermediate.
- The overall yield for the 16-step synthesis was 8.0%.
Conclusions:
- The described RCM and AD sequence provides an effective route to a key intermediate for amphidinolide T2 synthesis.
- This methodology contributes to the advancement of total synthesis strategies for complex macrolides.
