Treatment of acetylene with a suitable base affords lithium acetylide, which was used as a reagent in a partial synthesis of the antitumor natural product (+)-acutiphycin. (Org. Lett. 2014, 16, 1168-1171) Possible bases to consider H-C=C-H Acetylene Step 1 e Li :Base H-O: Li Lithium hydroxide (LiOH) Lithium acetylide three steps Draw the structure of lithium acetylide. Draw Your Solution Η Η Η Η II II H-Ċ-Ċ-Ċ-c: IIII Η Η Η Η Butyllithium (Buli) OR -CEC- Li OH CH3 -H CH3 Lithium diisopropyl amide (LDA) OMe O H3C H- H₂C e many steps HO OH (+)-Acutiphycin CH3 "OH CH3

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Treatment of acetylene with a suitable base affords lithium acetylide, which was used as a reagent in a partial synthesis of the
antitumor natural product (+)-acutiphycin. (Org. Lett. 2014, 16, 1168-1171)
Possible bases to consider
H-C=C-H
Acetylene
Step 1
Li :Base
T
H-O: Li
Lithium hydroxide (LiOH)
three steps
Lithium
acetylide
Draw the structure of lithium acetylide.
Draw Your Solution
di.
Η Η Η Η
| | | |
H-C-C-C-C:
II
HH HH
Butyllithium (BuLi)
OR
CEC-
Li
OH
CH3
-H
CH3
Lithium diisopropyl amide (LDA)
OMe
H3C
H
H₂C
many steps
Li
HO
OH
I
(+)-Acutiphycin CH3
CH₂
"OH
Transcribed Image Text:Treatment of acetylene with a suitable base affords lithium acetylide, which was used as a reagent in a partial synthesis of the antitumor natural product (+)-acutiphycin. (Org. Lett. 2014, 16, 1168-1171) Possible bases to consider H-C=C-H Acetylene Step 1 Li :Base T H-O: Li Lithium hydroxide (LiOH) three steps Lithium acetylide Draw the structure of lithium acetylide. Draw Your Solution di. Η Η Η Η | | | | H-C-C-C-C: II HH HH Butyllithium (BuLi) OR CEC- Li OH CH3 -H CH3 Lithium diisopropyl amide (LDA) OMe H3C H H₂C many steps Li HO OH I (+)-Acutiphycin CH3 CH₂ "OH
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