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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

Devise a synthesis of each compound from benzene. You may also use any organic compounds having four carbons or fewer, and any required inorganic reagents.

a.

b.

Synthesize each product from the given starting materials using an organocuprate coupling reaction.

Draw the structure of the two products of molecular formulaC15H26O2 formed when M is treated with Grubbs catalyst under high-dilution conditions.

Many variations of ring-closing metathesis have now been reported. Tandem ring-opening– ring-closing metathesis can occur with cyclic alkenes that contain two additional carbon– carbon double bonds. In this reaction, the cycloalkene is cleaved, and two new rings are formed. [1] What compounds are formed in this tandem reaction with the following substrates? [2] Devise a synthesis of the substrate in part (b) that uses a Diels–Alder reaction with diethyl maleate as the dienophile.

a.

b.

Sulfur ylides, like the phosphorus ylides of Chapter 21, are useful intermediates in organic synthesis. Methyl trans-chrysanthemate, an intermediate in the synthesis of the insecticide pyrethrin I (Section 26.4), can be prepared from diene A and a sulfur ylide. Draw a stepwise mechanism for this reaction.
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