Synthesis of Baconipyrone C

C29H44O8

Principal investigator	Ian Paterson
Publication year	2000
Synthesis type	Total
Number of steps	23 (3 parts)
References	Org. Lett. 2000, 2, 1513. Tetrahedron Lett. 1994, 35, 6925.

Part 1 of 3

Et3N, Cy2BCl

Et2O

-78 to 0 °C, 18.5 h, 100%

See the Aldol Addition

TBSOTf, 2,6-Lutidine

-78 °C, 99%

SmI2

THF

0 °C, 94%

Thexylborane
H2O2 , NaOH

H2O, THF

RT to 40 °C, 17 h, 59%

Et3N, DMSO, (COCl)2

CH2Cl2

-78 °C, 97%

See the Swern Oxidation

Pyr.HF

THF

0 °C, 60 min, 97%

Report an error in this part

Part 2 of 3

i-Pr2NEt, TiCl4

CH2Cl2

-78 °C, 2 h

See the Aldol Addition

2,6-Lutidine, TBSOTf

CH2Cl2

-78 °C, 2 h

i-Pr2NEt, TiCl4, EtCHO

CH2Cl2

-78 °C, 2 h

See the Aldol Addition

MeCN

20 °C, 2 h

Dess-Martin Periodinane

CH2Cl2

RT, 30 min, 60% (5 steps)

See the Dess-Martin Oxidation

Ph3P

CCl4, THF

RT, 3 d, 88%

H2, Pd/C

1 atm

EtOH

RT, 8 h, 95%

Dess-Martin Periodinane

CH2Cl2

RT, 90 min

See the Dess-Martin Oxidation

Sn(OTf)2, Et3N

CH2Cl2

-78 °C, 4.5 h, 74%

See the Aldol Addition

"Also isolated were 6% of other diastereomers"

SmI2, MeCHO

THF

-10 to -26 °C, 17 h, 100%

See the Evans-Tishchenko Reaction

TfOH, PMBOC(=NH)CCl3

Et2O

94%

n-Bu4N+ F-

THF

87%

K2CO3

MeOH

60 °C, 97%

(COCl)2, DMSO, Et3N

CH2Cl2

-78 to -30 °C, 5 h

See the Swern Oxidation

Na2HPO4, NaClO2, 2-Methyl-2-butene

H2O, t-BuOH

RT, 1 h, 96% (2 steps)

See the Pinnick-Lindgren Oxidation

Report an error in this part

Part 3 of 3

DMAP, 																	
																						Et3N, 																	
																						2,4,6-Trichlorobenzoyl chloride

																	PhMe															

								-78 to 0 °C, 								10 min, 								73%
							
								See the Yamaguchi Esterification
							
								"selectivity 91:09"

DDQ

pH=7 buffer

CH2Cl2

RT, 1 h, 67%

"Also isolated was 7% of C6-epimer"

Report an error in this part