Synthesis of Aplysin

Structure of Aplysin

C15H19BrO

Principal investigator	David C. Harrowven
Publication year	1999
Synthesis type	Total
Number of steps	11 (linear)
References	Tetrahedron Lett. 1999, 40, 4443.

Part 1 of 1

intermediate structure

ZrCl4

)))

CH2Cl2

RT, 24 h, 93%

See the Fries Rearrangement

intermediate structure

Me2SO4, KOH

Acetone

RT, 15 h, 97%

intermediate structure

S8, Morpholine

100 °C, 24 h, 76%

See the Willgerodt-Kindler Reaction

intermediate structure

MeI

H2O, THF

Reflux, 18 h, 90%

intermediate structure

4-Iodobutene, t-BuLi

THF

-78 to 0 °C, 5 h, 48%

intermediate structure

BCl3

CH2Cl2

0 °C to RT, 2 h, 81%

intermediate structure

i-PrN(Cy)Li
MeI

THF

-78 to 0 °C, 4 h, 84%

intermediate structure

Cp2TiCl2, AlMe3

PhMe

-78 to 0 °C, 6 h, 66%

See the Tebbe-Petasis Olefination

intermediate structure

(t-BuS)2

hν

Hexane(s)

RT, 24 h, 54%

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

intermediate structure

Ni (Raney)

EtOH

Reflux, 20 h, 74%

intermediate structure

Br2, Na2CO3

Petroleum ether

RT, 2 min, 75%

intermediate structure

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