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Named reactions

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Search synthesis

Aplysin

Chemical structure of Aplysin
C15H19BrO
Author David C. Harrowven
Publication year 1999
Synthesis type Total synthesis
Number of steps 11 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
ZrCl4
)))
CH2Cl2
RT, 24 h, 93 %

See the Fries Rearrangement
Chemical structure
Me2SO4, KOH
Acetone
RT, 15 h, 97 %
Chemical structure
Morpholine, S8
100 °C, 24 h, 76 %

See the Willgerodt-Kindler Reaction
Chemical structure
MeI
THF, H2O
Reflux, 18 h, 90 %
Chemical structure
t-BuLi, 4-Iodobutene
THF
-78 to 0 °C, 5 h, 48 %
Chemical structure
BCl3
CH2Cl2
0 °C to RT, 2 h, 81 %
Chemical structure
i-PrN(Cy)Li
THF
-78 to 0 °C, 4 h, 84 %
Chemical structure
Cp2TiCl2, AlMe3
PhMe
-78 to 0 °C, 6 h, 66 %

See the Tebbe-Petasis Olefination
Chemical structure
(t-BuS)2
Hexane(s)
RT, 24 h, 54 %

Also isolated was the C3-epimer (7 % yield).
Chemical structure
Ni (Raney)
EtOH
Reflux, 20 h, 74 %
Chemical structure
Br2, Na2CO3
Petroleum ether
RT, 2 min, 75 %
Chemical structure

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