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Chapter 26: Q 16. (page 1066)

What product is formed by ring-closing metathesis of compound V, a key intermediate in the synthesis of ingenol, a natural product mentioned in the chapter opener?

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01

Ring-closing metathesis

Metathesis reactions, such as ring-closing metathesis reactions, occur in dilute solutions. Several natural products are produced with the help of metathesis reactions.

02

Ingenol

Ingenol is familiar with another name known as Picato. This substance occurs in the plant named Euphorbia peplus. It is known to cause skin cancer.

03

Product formed by the ring-closing metathesis of compound V

Alkene metathesis leads to the exchange of double bonds of carbon atoms. The product formed in the reaction consists of a ring structure comprising a double bond. The reaction of compound V with the Grubbs catalyst can be given as follows.

Ring-closing metathesis of compound V

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Most popular questions from this chapter

Suzuki coupling of aryl iodide A and vinyl borane B affords compound C, which is converted to D in the presence of aqueous acid. Identify compounds C and D and draw a stepwise mechanism for the conversion of C to D.

Devise a synthesis of each of the following compounds. Besides inorganic reagents, you may use hydrocarbons and halides having ≤C’s, and CH2CHCOOCH3as starting materials. Each synthesis must use at least one of the carbon–carbon bond-forming reactions in this chapter.


b.

c.

d.

Draw the coupling product formed when each pair of compounds is treated with Pd(OAc)2, P(o-tolyl)3, and Et3N.

Treatment of cyclohexene with C6H5CHI2and Zn(Cu) forms two stereoisomers of molecular formula C13H16. Draw their structures and explain why two compounds are formed.

Bi-aryls, compounds containing two aromatic rings joined by a C-C bond, can often be efficiently made by two different Suzuki couplings; that is, either aromatic ring can be used to form the organoborane needed for coupling. In some cases, however, only one route is possible. With this in mind, synthesize each of the following bi-aryls using benzene as the starting material for each aromatic ring. When more than one route is possible, draw both of them. You may use any required organic or inorganic reagents.
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