Novel isoflavan–pterocarpan interconversions: some structural requirements for cyclization
- 1 January 1978
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 6,p. 224-225
- https://doi.org/10.1039/c39780000224
Abstract
Photolyses of pterocarpans in methanol and in acetic acid solutions provide novel synthetic access to 4-methoxy- and 4-acetoxy-2′-hydroxy-3,4-trans-isoflavans, respectively, and hence to 2′,4-dihydroxy-3,4-trans- analogues; easy, if not spontaneous, reversion of both 4-methoxy- and 4-hydroxyisoflavans to pterocarpans, compared with recalcitrant 2′-hydroxyisoflav-3-enes, indicates the significance of a suitable leaving group in the benzylic 4-position combined with a reduced heterocyclic ring at C-3 in promoting cyclization.Keywords
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