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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

Draw the products formed when each alkene is treated with Grubbs catalyst.

a.

b.

c.

What starting material is needed to synthesize each compound by a ring-closing metathesis reaction?

a.

b.

c.

What starting materials are needed to prepare each compound using a Heck reaction?

Devise a synthesis of each substituted cyclopropane. Use acetylene HC鈮�CH, as a startingmaterial in part (a), and cyclohexanone as a starting material in part (b). You may use anyother organic compounds and any needed reagents.

a.

b.

The reaction of cyclohexene with iodo-benzene under Heck conditions forms E, a coupling product with the new phenyl group on the allylic carbon, but none of the 鈥渆xpected鈥� coupling product F with the phenyl group bonded directly to the carbon鈥揷arbon double bond.

a. Draw a stepwise mechanism that illustrates how E is formed.

b. Step [2] in Mechanism 26.2 proceeds with syn addition of Pd and R' to the double bond.What does the formation of E suggest about the stereochemistry of the elimination reaction depicted in Step [3] of Mechanism 26.2?
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