a) The conversion of a-cyanoketone 1 to the cyclononanone 2 by treatment with a fluoride source, Appel conditions, and mildly basic conditions, respectively. NC OTBS OPMB O a) HF pyridine b) NBS, PPh3 c) DBU NC 2 O Highl OPMB

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a) The conversion of a-cyanoketone 1 to the cyclononanone 2 by treatment with a fluoride source, Appel
conditions, and mildly basic conditions, respectively.
NC
W
OTBS
MeN
OPMB
Me
b) The epimerization of this cis-fused tetracyclic enone to the trans-fused diastereomer (hint: think
'retro vinylogous Mannich reaction').
3
Me Me
10
NMe
a) HF pyridine
b) NBS, PPh3
c) DBU
H
NC
D₂0
D₂SO4 (cat.)
MeN
2
Me
OPMB
Me Me
H
4
Highli
NMe
Transcribed Image Text:a) The conversion of a-cyanoketone 1 to the cyclononanone 2 by treatment with a fluoride source, Appel conditions, and mildly basic conditions, respectively. NC W OTBS MeN OPMB Me b) The epimerization of this cis-fused tetracyclic enone to the trans-fused diastereomer (hint: think 'retro vinylogous Mannich reaction'). 3 Me Me 10 NMe a) HF pyridine b) NBS, PPh3 c) DBU H NC D₂0 D₂SO4 (cat.) MeN 2 Me OPMB Me Me H 4 Highli NMe
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