Synthesis of Upial

Structure of Upial

C15H20O3

Principal investigator	Michael J. Taschner
Publication year	1985
Synthesis type	Total
Number of steps	17 (linear)
References	J. Am. Chem. Soc. 1985, 107, 5570.

Part 1 of 1

intermediate structure

Li, NH3, BrCH2CO2Et

t-BuOH

80%

"83:17 d.r.; major isomer shown"

intermediate structure

KOH

EtOH, H2O

intermediate structure

Li, NH3

EtOH

intermediate structure

TsOH

PhH

RT, 53% (3 steps)

See the Fischer-Speier Esterification

intermediate structure

MeI, LDA

THF

83%

intermediate structure

LiAlH4

Et2O

99%

intermediate structure

(COCl)2, DMSO, Et3N

99%

See the Swern Oxidation

intermediate structure

Ph3P=CHOMe

THF

71%

See the Wittig Reaction

intermediate structure

HCl

DME, H2O, THF

RT, 70%

See the Aldol Addition

intermediate structure

MeMgBr

Et2O

0 °C, 95%

See the Grignard Reaction

intermediate structure

OsO4, NaIO4

75%

See the Lemieux-Johnson Oxidation

intermediate structure

KOCl

MeOH

0 °C, 87 %

See the Haloform Reaction

intermediate structure

(COCl)2, DMSO, Et3N

95%

See the Swern Oxidation

intermediate structure

Pyr, SOCl2

0 °C, 82%

intermediate structure

HCl, NaBH3CN

AcOH, H2O, THF

75%

intermediate structure

LDA
PhCH=CHCH2Br

HMPA, THF

64%

intermediate structure

OsO4, NaIO4

70%

See the Lemieux-Johnson Oxidation

intermediate structure

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