21) Intermediate Q was synthesized en route to analogs of a natural product has several protecting groups (A-E), some of which are orthogonal. The conditions listed below are used to selectively remove some of these protecting groups. 21a Fill in the groups (A-F) cleaved by the reagents indicated. 21b Draw the structure of the product that is formed when Q is treated with H2 and Pd/C. 21.1 Conditions Protecting Group (s) Removed DDQ Bu, Bu но ТВАF Bu o Bu NC H Pd/C TFA CN ТВАF DDQ TFA 21.2 H,C HN H Pd/C CH YCH, -Pr 1-Bu-si-o H,C OCH,

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t-Bu
21) Intermediate Q was synthesized en route to analogs of a natural product has several
protecting groups (A-E), some of which are orthogonal. The conditions listed below are
used to selectively remove some of these protecting groups.
21a Fill in the groups (A-F) cleaved by the reagents indicated.
21b Draw the structure of the product that is formed when Q is treated with H2 and Pd/C.
21.1 Conditions
Protecting Group (s) Removed
DDQ
Bu
Bu
IN.
Bu o Bu
но
TBAF
NC
H2 Pd/C
TFA
TBAF
CN
DDQ
TFA
H.
21.2
H,C
HN
H2 Pd/C
CH,
TCH,
.C
I-Pr
Hc F
t-Bu-
H,C
OCH,
Q
Transcribed Image Text:t-Bu 21) Intermediate Q was synthesized en route to analogs of a natural product has several protecting groups (A-E), some of which are orthogonal. The conditions listed below are used to selectively remove some of these protecting groups. 21a Fill in the groups (A-F) cleaved by the reagents indicated. 21b Draw the structure of the product that is formed when Q is treated with H2 and Pd/C. 21.1 Conditions Protecting Group (s) Removed DDQ Bu Bu IN. Bu o Bu но TBAF NC H2 Pd/C TFA TBAF CN DDQ TFA H. 21.2 H,C HN H2 Pd/C CH, TCH, .C I-Pr Hc F t-Bu- H,C OCH, Q
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