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Short Total Synthesis of (+)-Colletotryptins B-D and Mucronatin B Derivative
Wilailak Saetae1, Chayamon Chantana1, Saowanit Saithong2
1Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Burapha University, Chonburi 20131, Thailand.
The Journal of Organic Chemistry
|May 29, 2024
Summary
Researchers achieved the first total synthesis of colletotryptins and related compounds. This efficient method utilizes a novel stereoselective transindolylation, offering a modular strategy for synthesizing these indole-containing natural products.
Area of Science:
- Organic Chemistry
- Natural Product Synthesis
- Medicinal Chemistry
Background:
- Colletotryptins and mucronatin B are natural products belonging to the 3-(indol-2-yl)-3-(indol-3-yl)-1,2-propanediol (IIPDO) class.
- These compounds possess two stereogenic centers and are isolated from fungal and plant sources.
- Previous synthetic routes for these complex molecules were limited or unavailable.
Purpose of the Study:
- To achieve the first total synthesis of (+)-colletotryptins B-D, ent-colletotryptin A, and a diastereomer of mucronatin B.
- To develop an efficient and modular synthetic strategy for IIPDO analogues.
- To explore a novel stereoselective catalytic method for constructing the core IIPDO scaffold.
Main Methods:
- A two-step and three-step total synthesis was designed for the target natural products.
- Key step involves a bismuth(III) triflate (Bi(OTf)3)-catalyzed stereoselective transindolylation reaction.
- The synthesis utilizes (S)-3,3'-di(1H-indol-3-yl)propane-1,2-diol as a precursor.
Main Results:
- Successful and first total synthesis of (+)-colletotryptins B-D, ent-colletotryptin A, and a diastereomer of mucronatin B.
- Overall yields ranged from 28% to 54% across the synthetic routes.
- The Bi(OTf)3-catalyzed reaction demonstrated high stereoselectivity and efficiency.
Conclusions:
- A concise and modular synthetic strategy for IIPDO analogues has been established.
- The developed method is operationally simple, uses an environmentally friendly catalyst, and tolerates various functional groups.
- This approach is suitable for both academic research and industrial applications in natural product synthesis.
