Journal of the American Chemical Society p. 7854 - 7858 (1988)
Update date:2022-07-31
Topics:
Andrews, Robert C.
Teague, Simon J.
Meyers, A. I.
Using a diastereoselective addition of the appropriate aryllithium to a naphtalene-containing chiral oxazoline leads to advanced intermadiate 11 in the podophyllotoxin series.The latter is obtained in a 92:8 de.Transformation of the oxazoline moiety to the requisite lactone 18 followed by invoking the Kende route to the target gave natural (-)-podophyllotoxin in 94 percent ee.The overall yield of the sequence, accomplished in 24 steps, was 5 percent.
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