Part A How many ether functional groups are present in Bryostatin 1? Express you

Question

Part A

How many ether functional groups are present in Bryostatin 1?

Express your answer as an integer.

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Part B

Identify the other oxygen-containing functional groups.

Check all that apply.

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Part C

This is called a macrolide because it contains a large number of atoms in the large ring. How many atoms are in the large ring?

Express your answer as an integer.

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Part D

How many chiral centers are in this molecule?

Express your answer as an integer.

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Part E

Using the number of chiral centers you reported in Part D, calculate the number of stereoisomers possible at these chiral centers. (Ignore stereoisomers at double bonds.)

Express your answer as an integer.

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One of the crowning achievements of natural products synthesis was Bryostatin 1, published by Professor Gary Keck (University of Utah; Journal of the American Chemical Society, 2011, 133, 744-747). The Bryostatins are a family of compounds isolated from aquatic invertebrates known as Bryozoans. The compounds are of interest for a variety of biological effects, including anti-cancer activity and reversing brain damage in rodents.

Part A

How many ether functional groups are present in Bryostatin 1?

Express your answer as an integer.

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Part B

Identify the other oxygen-containing functional groups.

Check all that apply.

Check all that apply. alcohols esters peroxides aldehydes ketones carboxylic acids

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Part C

This is called a macrolide because it contains a large number of atoms in the large ring. How many atoms are in the large ring?

Express your answer as an integer.

atoms

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Part D

How many chiral centers are in this molecule?

Express your answer as an integer.

chiral centers

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Part E

Using the number of chiral centers you reported in Part D, calculate the number of stereoisomers possible at these chiral centers. (Ignore stereoisomers at double bonds.)

Express your answer as an integer.

possible stereoisomers

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HO O O O /0 O OH O Bryostatin 1 OH H O O OH O O OI-11'?

Explanation / Answer

part A

ether functiona groups = 3

part B

ester

alchol

part C

large ring contains 5 c-atoms , 1-O-atoms = 6-atoms

part D

number of chiral centers = 9

part E

number stereo isomers = 2^n = 2^9 = 512

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