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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

Question: A difficult problem in the synthesis of PGF2ฮฑ is the introduction of the OH group at C15 in the desired configuration.

  1. Label this stereogenic center as R or S.
  2. A well known synthesis of PGF2ฮฑinvolves reaction of A with Zn(BH4)2, a metal hydride reagent similar in reactivity to NaBH4, to form two isomeric products, B and C. Draw their structures and indicate their stereochemical relationship.
  3. Suggest a reagent to convert A to the single stereoisomer X.

Treatment of cholesterol with mCPBA results in formation of a single epoxide A, with the stereochemistry drawn. Why isnโ€™t the isomeric epoxide B formed to any extent?

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

Question: 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?

Draw the enantiomer and any two diastereomers of cholesterol. Does the OH group of cholesterol occupy an axial or equatorial position?
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