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Chapter 31: Q41P (page 1260)

Farnesyl diphosphate is cyclized to sesquiterpene A, which is then converted to the bicyclic product epi-aristolochene. Write a stepwise mechanism for both reactions.

Short Answer

Expert verified

Answer

The mechanism of the reaction

Step by step solution

01

About farnesyl diphosphate

The commonly used intermediate used for the biosynthesis of terpenes, sterols, terpenoids, carotenoids, etc., is farnesyl diphosphate.

This compound is also used in the synthesis of the part present in the electron transport chain known as CoQ.

02

About epi-aristolochene

The formed product epi-aristolochene is an enzyme. This compound is mainly used in the plant metabolite. This compound exists naturally in the Nicotiana tabacum. This compound is a member of octa hydro naphthalenes.

03

About the mechanism

The given starting material is rearranged and written similarly to the cyclic form. The OPP is removed, and the cation is obtained, which is resonance stabilized. Then it is treated with an acid that leads to the formation of a cation.

Then it is subjected to a 1,2 H shift followed by 1,2-CH3shift. On rearrangement, the final product is obtained. The mechanism is shown below.

The mechanism of the reaction

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Most popular questions from this chapter

An isoprene unit can be thought of as having a head and a tail. The “head” of the isoprene unit is located at the end of the chain nearest the branch point, and the “tail” is located at the end of the carbon chain farthest from the branch point. Most isoprene units are connected together in a “head-to-tail” fashion, as illustrated. For both lycopene (Problem 31.26), and squalene (Figure 31.9), decide which isoprene units are connected in a head-to-tail fashion and which are not.

Draw three-dimensional structures for each alcohol. Label the OH groups as occupying axial or equatorial positions.

a.

b.

c.

d.

Classify each terpene and terpenoid in Problem 31.26 (e.g., as a monoterpene, sesquiterpene, etc.).

The biosynthesis of lanosterol from squalene has intrigued chemists since its discovery. It is now possible, for example, to synthesize polycyclic compounds from acyclic or monocyclic precursors by reactions that form several C-C bonds in a single reaction mixture.

  1. Draw a stepwise mechanism for the following reaction.
  2. Show how X can be converted to 16, 17-dehydroprogesterone. (Hint: See Figure 24.5 for a related conversion.)

Explain why regularly ingesting a large excess of a fat-soluble vitamin can lead to severe health problems, whereas ingesting a large excess of a water-soluble vitamin often causes no major health problems.
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