Synthesis of Englerin A

C26H34O6

Principal investigator	William J. Chain
Publication year	2011
Synthesis type	Total
Number of steps	9 (3 parts)
References	J. Am. Chem. Soc. 2011, 133, 6553.

Part 1 of 3

LDA

THF

-78 °C to RT, 8.5 h, 89%

See the Claisen Condensation

DBU

THF

RT, 12 h, 72%

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Part 2 of 3

Grubbs catalyst (2nd gen.)

CH2Cl2

Reflux, 48 h, 99%

See the Olefin Metathesis

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Part 3 of 3

LDA

																	THF															

								-78 °C to RT, 								2 h, 								75%
							
								See the Michael Addition
							
								"66:33 dr"

SmI2

HMPA, THF

RT, 3 h, 43%

DMAP, Et3N

PhMe

RT, 2 d, 86%

See the Yamaguchi Esterification

NaBH4

MeOH

0 °C, 30 min, 100%

TMS2NLi
(imid)2SO2

-10 °C to RT, 12.5 h, 100%

18-Crown-6

PhMe

Reflux, 36 h, 74%

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