The Research Group Gets Started!

Five days later.

On the fourth floor of the USTC Medical Center building, in a medicinal chemistry laboratory.

At this moment, Xu Yun stood at the operating table in a pure cotton lab coat, facing six men and women of varying heights.

"Junior students, now that everyone's here, I'll just say half a chapter. Cough, cough, a few words."

Xu Yun waved a stapled stack of documents in his hand, his gaze quickly sweeping over the people in front of him:

"Yesterday morning, I received the project approval receipt. Now that we have the procedures, venue, and personnel sorted out, our project group is officially established.

This project group has no supervisor. I am the applicant and the primary responsible person. The laboratory usage period is two weeks. Your participation will be recorded in your files. Regardless of the outcome, it will be a decent addition to your resume and should be somewhat helpful for your future."

Upon hearing this, two of the six people in front of him couldn't suppress a hint of joy.

USTC, as one of the C9 League universities, has an annual R&D budget of just over ten billion yuan, ranking around ninth or tenth in the country.

While this number seems large, after deducting funds for various programs like the 973 Program, 863 Program, National Science and Technology Support Program, and International Science and Technology Cooperation and Exchange Special Fund, the budget and quota allocated to each department are far less than they appear.

Then, after being divided among the big names and experts, while there might still be some budget remaining, there aren't many high-quality project slots left.

Many graduate students work for a semester or two without even getting close to a major project, only to be exploited by their supervisors like beasts of burden.

Therefore, when Xu Yun approached them with the project approval letter for Tian Liangwei's auxiliary project, the struggling graduate students immediately nodded enthusiastically, their heads shaking so vigorously it was like a massage wand, almost making Xu Yun say "Huaxia people don't lie to Huaxia people."

Frankly speaking, having participated in a project group of this caliber, regardless of whether any results are produced, one can ask for at least an extra five hundred yuan per month when applying for salary after graduation!

Xu Yun paused for a moment and continued:

"Our project's goal is simple: to attempt to synthesize a new substance by combining pheromones and third-generation Imidacloprid, to verify and explore the direction of fourth-generation Imidacloprid. The ultimate goal is..."

As soon as he finished speaking, the junior students collectively shouted:

"Exterminate the cockroaches!"

After saying that, everyone burst into laughter.

Amidst the laughter, a girl with short hair raised her hand and asked Xu Yun curiously:

"Senior, why do you have such a strong resentment towards cockroaches?"

Xu Yun glanced at her lightly. This girl was Tang Yiqiu, a senior undergraduate student with good grades and a good reputation:

"It's a sad story for me, but it would make you very happy to hear, so I refuse to answer."

He then waved the documents in his hand, the pages rustling in the air:

"Alright, enough idle talk. We have limited time. Everyone check your gas masks and organic vapor cartridges, and put on your protective skirts. We'll start the experiment in fifteen minutes!"

Then he gave Qiu Sheng a look:

"Old Qiu, check the machines and the circuit breakers. I'll go distribute the materials."

Qiu Sheng nodded:

"Understood."

Fifteen minutes later, all preparations were complete.

The main experimental reagents for Xu Yun and the others this time included 2-phenylpyridine, 4-(hydroxymethyl)phenylboronic acid, 2-naphthaleneboronic acid, 3-furanylboronic acid, 3-benzothienylboronic acid, N-phenylpyrazole, benzoquinoline, [Ru(p-cymene)2Cl2]2, and so on.

In addition, there were over thirty other reagents, including 2-bromopyridine, 2-bromo-4-chloropyridine, THF, DMF (N,N-dimethylformamide), DMSO, 1,4-dioxane, etc. (I've written the specifics in the author's notes.)

Meanwhile, the rest of the group also took their positions one by one.

"To combine pheromones and Imidacloprid, we first need to cyclize the CH3. I plan to achieve this through a hydrogenation reduction reaction of epoxy alkyne coupled with 1-bromo-2-pentyne."

At the operating table, Xu Yun explained his idea while addressing a tool, no, a junior student:

"Li Yi, this task is yours."

"Understood!"

Li Yi, whom Xu Yun mentioned, was a graduate student, 24 years old, with a buzz cut. Upon hearing this, she immediately began the operation.

At the same time, Xu Yun looked at Tang Yiqiu again:

"Xiao Tang, you're responsible for the follow-up. Try to capture the optically active fragment of the epoxy sulfonate ester!"

"Understood!"

As everyone knows.

Allyl alcohol, catalyzed by isopropyl L-(+)-tartrate and titanium tetraisopropoxide, undergoes the Sharpless asymmetric epoxidation reaction to yield (2S,3R)-2,3-epoxy-1-tetradecanol.

The epoxy alcohol (2S,3R)-9, after tosylation and perchloric acid ring opening, inverts the absolute configuration of the carbon atom at position 3 from R to S, yielding (2S,3S)-2,3-dihydroxy-1-tetradecyl p-toluenesulfonate; then, through potassium carbonate cyclization and tosylation, (2S,3S)-1,2-epoxy-3-tetradecyl p-toluenesulfonate can be obtained with a yield of 89%.

It's very simple and easy to understand.

A few minutes later, Tang Yiqiu raised her hand again, but this time she wasn't asking Xu Yun why he hated cockroaches:

"Senior, the epoxy sulfonate ester has been captured!"

"Excellent, what's the ee value?"

"Still determining. The epoxy alcohol and dinitrobenzoyl chloride are still reacting. Oh, it's out, 93%!"

Upon hearing this, Xu Yun let out a slight sigh of relief.

The so-called ee value refers to enantiomeric excess. The theoretical ee value for the chiral epoxy sulfonate ester is 90%. The 93% measured by Xiao Tang is above the standard line, marking the first successful step.

After completing the synthesis of the key optically active intermediate, the next step is to study the asymmetric synthesis of the target pheromone.

This step involves reacting the epoxy sulfonate ester with trimethylsilylacetylene to achieve epoxy ring opening, followed by treatment with potassium carbonate for ring closure and desilylation, yielding (4S,5R)-4,5-epoxy-1-hexadecyne. The yield for this step is 60%.

That's right, 89% for the first step and 60% for the second.

A yield that's nearly halved.

This is a very common situation in biochemistry: the yield decreases as you progress, from 90% to 60%, then to 30%.

After seven or eight rings, the yield for highly unusual compounds might even drop to single digits.

This is why research is said to be expensive—in the mere ten minutes Xu Yun and the others had been working, including machine wear and tear, at least 1,000 yuan had already been spent, a whole alliance leader's worth.

The preparation of 5-epoxy-1-hexadecyne went smoothly. Just as Xu Yun and the others were preparing to take another step forward, another graduate student responsible for nucleophilic substitution suddenly exclaimed, sighing, "Senior, the nucleophilic substitution reaction failed."

All experimental reagents:

2-phenylpyridine, p-tolylboronic acid, p-vinylphenylboronic acid, 4-(hydroxymethyl)phenylboronic acid, 4-vinylphenylboronic acid, 2-naphthylboronic acid, 3-furylboronic acid, 3-benzothienylboronic acid, N-phenylpyrazole, benzoquinoline, [Ru(p-cymene)2Cl2]2.

As well as paraformaldehyde, DCM (dichloromethane), DCE, CHCl3 (chloroform), MeOH (methanol), EtOH (ethanol), EtOAc (ethyl acetate), THF (tetrahydrofuran), DMF (N,N-dimethylformamide), DMSO (dimethyl sulfoxide), 1,4-dioxane, CH3CN (acetonitrile), n-hexane, and toluene, among others.

2-bromopyridine, 2-bromo-4-chloropyridine, 2-bromo-3-methylpyridine, 2-bromo-5-methylpyridine, 2-bromo-3-fluoropyridine,