1 Oxirane (ethylene oxide) YSU YSU Brevetoxin B YSU YSU 2 - - PDF document

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1 Oxirane (ethylene oxide) YSU YSU Brevetoxin B YSU YSU 2 - - PDF document

YSU YSU YSU YSU 1 Oxirane (ethylene oxide) YSU YSU Brevetoxin B YSU YSU 2 Palytoxin Palytoxin YSU YSU Mucocin YSU YSU 3 YSU YSU YSU YSU 4 YSU YSU Chapters 6 & 15 YSU YSU 5 Sequential acid base & S N 2


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SLIDE 1

1

YSU YSU YSU YSU

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SLIDE 2

2

YSU YSU Oxirane (ethylene oxide) YSU YSU

Brevetoxin B

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SLIDE 3

3

Palytoxin

YSU YSU

Palytoxin Mucocin

YSU YSU

slide-4
SLIDE 4

4

YSU YSU YSU YSU

slide-5
SLIDE 5

5

YSU YSU YSU YSU

Chapters 6 & 15

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SLIDE 6

6

YSU YSU

Sequential acid‐base & SN2 reactions

YSU YSU

Sequential protonation & SN2 reactions

slide-7
SLIDE 7

7

Epoxidation ‐ intermolecular

O O OH Cl

CH Cl O YSU YSU Substitution ‐ intramolecular CH2Cl2 OH Br O

NaOH, solvent

SN

N2

2 Control Control

YSU YSU

Similar to SN2 reaction; stereocenters inverted

slide-8
SLIDE 8

8

SN1 Control 1 Control

YSU YSU YSU YSU

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SLIDE 9

9

YSU YSU

Acid‐base reaction followed by SN2 displacement

Not covering 16 16 and 16 17

YSU YSU

Not covering 16.16 and 16.17