Aplysin

C₁₅H₁₉BrO

Part 1 of 1

ZrCl₄
)))

CH₂Cl₂
RT, 24 h, 93 %

See the Fries Rearrangement

Me₂SO₄, KOH

Acetone
RT, 15 h, 97 %

Morpholine, S₈

100 °C, 24 h, 76 %

See the Willgerodt-Kindler Reaction

MeI

THF, H₂O
Reflux, 18 h, 90 %

t-BuLi, 4-Iodobutene

THF
-78 to 0 °C, 5 h, 48 %

BCl₃

CH₂Cl₂
0 °C to RT, 2 h, 81 %

i-PrN(Cy)Li

THF
-78 to 0 °C, 4 h, 84 %

Cp₂TiCl₂, AlMe₃

PhMe
-78 to 0 °C, 6 h, 66 %

See the Tebbe-Petasis Olefination

(t-BuS)₂
hν

Hexane(s)
RT, 24 h, 54 %

Also isolated was the C3-epimer (7 % yield).

Ni (Raney)

EtOH
Reflux, 20 h, 74 %

Br₂, Na₂CO₃

Petroleum ether
RT, 2 min, 75 %