Accidental discoveries

Chemistry Level pending

The discovery of Penicillin was a turning point in human history. Derived form the the fungal species of Penicillium, it has kept bacteria from taking millions of human lives. We now face a new enemy that threatens to surpass bacteria's death toll. Can the same fungal family save humanity from cancer?

Aspergillus fumigatus produces two different types of metabolites that are known to have anti-cancerous properties. They are derived form the same precursor M in a bio-synthetic manner:

X can be thought of as a dehydrated isomer of Z. They are the products of conjugate and direct addition respectively.

Compound C and X share a similar type of molecular structure and was derived from A that can be generated using the following reaction: (Ts is the tosyl group)

This reaction was further improved when a key component of Cytochrome was used. This component (F) can be described as a five membered aromatic heterocycle that contains four distinct H-NMR signals and three 13-C NMR signals. This component is used as a base in many reactions :

A reacts with the ylide shown below to form B by expelling \(Ph_{3}PO\) and \(SO_{2}\).

B is difficult to isolate as it transforms into C on heating.

We define certain quantities:

  • \(\alpha\) is the number of amide groups in X
  • \(\beta\) is the number of rings in C

Calculate \(\alpha +\beta\)


  • Deduce the structure of X and provide a plausible mechanism for the dehydration process.
  • Deduce structures of compounds A-C
  • What molecular structure do C and X share?

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