Related Experiment Video
Updated: Jun 3, 2026

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
Published on: November 9, 2019
Total synthesis of hoiamide C
Lei Wang1, Zhengshuang Xu, Tao Ye
1Laboratory of Chemical Genomics, Peking University Shenzhen Graduate School, University Town of Shenzhen, Xili, Nanshan District, Shenzhen, China.
Researchers synthesized Hoiamide C in 16 steps, achieving a 1.8% yield. This synthesis unambiguously confirmed the complex natural product
Area of Science:
- Organic Chemistry
- Natural Product Synthesis
Background:
- Hoiamide C is a complex natural product.
- Its structural elucidation and synthesis are of significant interest.
Purpose of the Study:
- To achieve the total synthesis of Hoiamide C.
- To unambiguously confirm the proposed structure of Hoiamide C through synthesis.
Main Methods:
- Multi-step organic synthesis.
- Utilized homoallylic alcohol 18 as a starting material.
Main Results:
- Successful synthesis of Hoiamide C in 16 steps.
- Achieved an overall yield of 1.8% for the synthetic route.
- The synthesized compound's data unequivocally confirmed the structure.
Conclusions:
- The total synthesis of Hoiamide C was accomplished.
- The synthetic route provides unambiguous structural confirmation.
- This work contributes to the field of natural product synthesis.
Related Concept Videos
Preparation of Amides
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
Preparation of Alkynes: Dehydrohalogenation
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
Preparation of 1° Amines: Gabriel Synthesis
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Acid Halides to Amides: Aminolysis
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
Electrophilic Addition to Alkynes: Halogenation
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
Multiple Halogenation of Methyl Ketones: Haloform Reaction

