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A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
Published on: October 4, 2019
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Total Synthesis of Terpioside B
Kazuki Inaba1, Masato Endo1, Naoto Iibuchi1
1Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan.
Chemistry (Weinheim an Der Bergstrasse, Germany)
|June 23, 2020
Summary
The total synthesis of terpioside B was achieved, overcoming challenges in creating specific glycosidic linkages. This breakthrough utilized novel boron-mediated aglycon delivery and remote group-assisted glycosylation methods.
Area of Science:
- Organic Chemistry
- Carbohydrate Chemistry
- Synthetic Chemistry
Background:
- Terpioside B is a complex natural product requiring advanced synthetic strategies.
- The construction of specific glycosidic linkages, particularly 1,2-cis-glycosidic bonds, presents a significant synthetic challenge.
Purpose of the Study:
- To achieve the first total synthesis of terpioside B.
- To develop and apply novel methodologies for stereoselective glycosylation.
Main Methods:
- Stereoselective installation of challenging 1,2-cis-glycosidic linkages.
- Boron-mediated aglycon delivery (BMAD) for α(1,4)-linked d-galactoside construction.
- Remote group-assisted glycosylations for simultaneous α-l-fucofuranoside synthesis.
Main Results:
- Successful total synthesis of terpioside B (1).
- Efficient construction of an α(1,4)-linked d-galactoside using the BMAD method.
- Stereoselective and simultaneous synthesis of α-l-fucofuranosides.
Conclusions:
- The developed synthetic route provides a viable pathway to terpioside B.
- The employed glycosylation strategies are effective for constructing complex carbohydrate structures.
- This work advances the field of total synthesis and carbohydrate chemistry.
