A new synthesis of podophyllum lignans by Weitz' aminium salt-induced free radical cycloaddition reaction of a doubly unsaturated ester

DOI: 10.1248/cpb.43.1977

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 1977 - 1984 (1995)

Update date:2022-08-03

Topics:

Authors:

Ara Ara

Takeya Takeya

Tobinaga

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Article abstract of DOI:10.1248/cpb.43.1977

(±)-Isopodophyllotoxin (1e) and related lactones 12, 13, 14 were synthesized by a biomimetic procedure from the doubly unsaturated esters 11a and 11b by means of an oxidative free radical cycloaddition reaction utilizing a stable cation radical salt, Weitz' aminium salt, in one step. (±)-Isopicropodophyllin (1g), the trans-fused lactones, 12, 13, and 16, and the cis-fused lactone 17 were also synthesized from the esters 11c and 11d by the reaction with the same reagent.

Full text of DOI:10.1248/cpb.43.1977

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