Synthesis of podophyllotoxin

1 January 1989

journal article
research article
Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications

No. 18,p. 1370-1371
https://doi.org/10.1039/c39890001370

Abstract

The alkene (2) obtained directly from the reaction of dimethyl maleate with the pyrone (1) is converted into (±)-podophyllotoxin (12) in seven steps and 24% overall yield; novel steps include the epimerisation of (9) at C-3 using 1,8-diazabicyclo[5.4.0]undec′7-ene (DBU) and selective oxidation of (8) to (9) using (Buⁿ ₃Sn)₂O–I₂.

Keywords

OBTAINED DIRECTLY
ALKENE
PODOPHYLLOTOXIN
STEPS INCLUDE
DIMETHYL MALEATE
NOVEL STEPS
SEVEN STEPS
SELECTIVE OXIDATION
PYRONE

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