Synthesis of Aigialomycin D

Structure of Aigialomycin D

C18H22O6

Principal investigator	Joanne E. Harvey
Publication year	2009
Synthesis type	Total
Number of steps	20 (3 parts)
References	J. Org. Chem. 2009, 74, 2271.

Part 1 of 3

intermediate structure

NaH
n-BuLi

THF

-78 °C to Reflux, 51 h, 40%

intermediate structure

Ac2O, Et3N

CH2Cl2

RT, 12 h, 98%

intermediate structure

Bz2O2, NBS

CCl4

Reflux, 6 h, 71%

See the Wohl-Ziegler Reaction

intermediate structure

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Part 2 of 3

intermediate structure

HCl

Acetone, MeOH

Reflux, 8 h, 55%

intermediate structure

TsCl

Pyr

0 °C to RT, 15 h, 84%

intermediate structure

NaI

MEK

Reflux, 24 h, 99%

See the Finkelstein Reaction

intermediate structure

Zn, AcOH

MeOH

Reflux, 8 h

intermediate structure

+

intermediate structure

MeOH

0 °C to RT, 12 h, 74% (2 steps)

See the Wittig Reaction

intermediate structure

Cyclohexene, NaBH4, CuCl

MeOH

-78 °C, 60 min, 96%

intermediate structure

LiAlH4

Et2O

-10 °C, 10 min, 97%

intermediate structure

MsCl, Et3N, DMAP

CH2Cl2

0 °C to RT, 12 h, 97%

intermediate structure

KSAc

DMF

0 °C to RT, 12 h, 90%

intermediate structure

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Part 3 of 3

intermediate structure

+

intermediate structure

K2CO3

MeOH

RT, 12 h, 86%

intermediate structure

NaH, MeOCH2Cl

DMF

0 °C to RT, 2 h, 74%

intermediate structure

KOH

H2O, MeOH

90 °C, 48 h, 98%

intermediate structure

+

intermediate structure

Ph3P, DIAD

THF

0 °C to RT, 2.5 h, 94%

See the Mitsunobu Reaction

intermediate structure

mCPBA

CH2Cl2

0 °C to RT, 2 h, 84%

intermediate structure

Grubbs-Hoveyda catalyst (2nd gen.)

µW

CH2Cl2

75 °C, 30 min, 86%

See the Olefin Metathesis

intermediate structure

CCl4, KOH

CH2Cl2, t-BuOH

RT to 35 °C, 32 min, 84%

See the Ramberg-Bäcklund Reaction

intermediate structure

HCl

H2O, MeOH

RT, 3 d, 85%

intermediate structure

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