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Chapter 31: Q31P (page 1259)

Flexibilene is a terpene isolated from Sinulariaflexibilis, a soft coral found in the Indian Ocean. Draw a stepwise mechanism for the formation of flexibilene from farnesyl diphosphate and isopentenyl diphosphate. What is unusual about the cyclization that forms the 15-membered ring of flexibilene?

Short Answer

Expert verified

The unusual feature of the cyclization is the generation of 2o carbocation instead of

3o carbocation.

Step by step solution

01

Flexibilene

Flexibilene is a diterpene with a chemical formula C20H32 , and its structure has a 15-membered ring. It is obtained from farnesyl diphosphate and isopentenyl diphosphate.

02

Stepwise mechanism of flexibilene 

The unusual feature of cyclization is the generation of 2o carbocation instead of 3o carbocation. The cyclization at the other end of the C=C bond will give 3o carbocation, and a 14-membered ring will be formed.

Moreover, the rearrangement of 2o carbocation into 3ocarbocation does not occur.

Stepwise mechanism of flexibilene

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Most popular questions from this chapter

Draw all possible constitutional isomers of a triacylglycerol formed from one mole each of palmitic, oleic, and linoleic acids. Locate the tetrahedral stereogenic centers in each constitutional isomer.

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