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11 .OPP OPP 11 farnesyl pyrophosphate nerolidyl pyrophosphate 1 epi-cedrol OH I, 3 2 +

Introduction to General, Organic and Biochemistry

11th Edition

ISBN:9781285869759

Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres

Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres

Chapter31: Immunochemistry

Section: Chapter Questions

Problem 31.75P

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Question

the cyclization of a farnesyl pyrophosphate to give epi-cedrol,

A. Provide a stepwise mechanism for the formation of nerolidyl pyrophosphate from farnesylpyrophosphate

B. Provide a stepwise mechanism for the formation of carbocation 1 from nerolidyl pyrophosphate. Number the backbone carbons of nerolidyl pyrophosphate from 1 to 11 as shown, and include the carbon numbering in your structure of 1

C. Following from B, give an arrow-pushing mechanism to convert 1 to 2 and 2 to 3. Use the backbone carbon numbering from 1 to indicate where carbon atoms ended up in 2 and 3

D. In addition to forming epi-cedrol, carbocation 3 gives three minor byproducts: a diastereomeric alcohol and two alkenes. Draw mechanisms that could give rise to these three products

11
.OPP
OPP
11
farnesyl pyrophosphate
nerolidyl pyrophosphate
1
epi-cedrol
OH
I,
3
2
+

Definition Definition Organic compounds that contain at least one double bond between carbon-carbon atoms. The general molecular formula for alkenes with one double bond is C n H 2n .

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