Synthesis of Daphnilactone A

C23H35NO2

Principal investigator	Clayton H. Heathcock
Publication year	1989
Synthesis type	Total
Number of steps	12 (2 parts)
References	J. Am. Chem. Soc. 1989, 111, 1530. J. Org. Chem. 1992, 57, 2585.

Part 1 of 2

Br2, P (Red)

50 °C, 12.5 h, 82%

See the Hell-Volhard-Zelinsky Reaction

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Part 2 of 2

i-Pr2NLi

THF

-78 to 0 °C, 4 h, 85%

LiAlH4

Et2O

0 °C to RT, 60 min, 96%

Pyr

CH2Cl2

0 °C, 10 min, 95%

Na.Naphthalene, ZnCl2

HMPA, THF

0 °C to RT, 9 h, 89%

See the Reformatsky Reaction

LiAlH4

Et2O

RT, 6 h, 90%

Et3N, DMSO, (COCl)2

CH2Cl2

-78 to 0 °C, 90 min

See the Swern Oxidation

NH3

																	CH2Cl2															

								0 °C to RT, 								60 min, 								47% (2 steps)
							
								See the Diels-Alder Reaction
							
								See the Ene Reaction