Oligomeric flavanoids. Part W. Base-catalyzed pyran rearrangements of procyanidin B 2, and evidence for the oxidative transformation of B- to A-type procyanidins

DOI: 10.1016/S0040-4020(01)87771-1

Source and publish data:

Tetrahedron p. 5733 - 5740 (1990)

Update date:2022-07-29

Topics:

Authors:

Burger, Johann F. W.

Kolodziej, Herbert

Hemingway, Richard W.

Steynberg, Jan P.

Young, Desmond A.

Ferreira, Daneel

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Article abstract of DOI:10.1016/S0040-4020(01)87771-1

Procyanidin B-2 3 is subject to facile C-ring isomerizations in 0.1M NaHCO₃ solution to form a novel series of 3,4,9, 10-tetrahydro-2H, 8-pyrano[2,3-h]chromenes 7, 9, and 10. The low percentage conversion of B- to A-type procyanidin 2 is rationalized in terms of an initial oxidative removal of hydride ion at C-2 (C-ring).

Full text of DOI:10.1016/S0040-4020(01)87771-1

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