Synthesis of Epolactaene

Structure of Epolactaene

C21H27NO6

Principal investigator	Yujiro Hayashi
Publication year	2002
Synthesis type	Total
Number of steps	20 (linear)
References	J. Org. Chem. 2002, 67, 9443.

Part 1 of 1

intermediate structure

+

intermediate structure

PhH

90 °C, 90 min, 98%

See the Wittig Reaction

intermediate structure

Imidazole, TBSCl

CH2Cl2, DMF

RT, 20 min, 99%

intermediate structure

i-Bu2AlH

CH2Cl2

0 °C, 60 min

intermediate structure

DMSO, Et3N, Pyr.SO3

CH2Cl2

0 °C, 90 min, 94% (2 steps)

See the Parikh-Doering Oxidation

intermediate structure

+

intermediate structure

NaH

THF

0 °C to RT, 60 min, 96%

See the Horner-Wadsworth-Emmons Reaction

intermediate structure

i-Pr2NLi
MeCHO

HMPA, THF

-78 °C, 4.5 h, 96%

See the Aldol Addition

intermediate structure

DMAP, Et3N, MsCl

CH2Cl2

0 °C to RT, 90 min

intermediate structure

DABCO

MeOH

100 °C, 5 d, 86% (2 steps)

intermediate structure

n-Bu4N+ F-

THF

0 °C, 3 h, 100%

intermediate structure

Pyr.SO3, Et3N, DMSO

CH2Cl2

0 °C, 90 min, 100%

See the Parikh-Doering Oxidation

intermediate structure

+

intermediate structure

n-BuLi

DME

0 °C to RT, 40 min, 100%

See the Horner-Wadsworth-Emmons Reaction

intermediate structure

n-BuLi, MeCN

THF

-88 to -78 °C, 60 min, 93%

See the Claisen Condensation

intermediate structure

CF3CO2H

CH2Cl2

0 °C to RT, 20 min

intermediate structure

CH2N2

Et2O

-78 °C, 92% (2 steps)

intermediate structure

+

intermediate structure

(CH2NH2)2.2AcOH

PhH

RT, 2 h

See the Knoevenagel Condensation

intermediate structure

n-BuLi, Ph3COOH

THF

-78 °C, 2 h

See the Michael Addition

intermediate structure

AcOH, NH4F

H2O, THF

RT, 90 min

intermediate structure

SiO2

EtOAc, Hexane(s)

intermediate structure

NH3

H2O, MeOH

0 °C, 30 min, 22% (5 steps)

intermediate structure

DMSO, Et3N, Pyr.SO3

CH2Cl2

0 °C, 2 h, 78%

See the Parikh-Doering Oxidation

intermediate structure

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