Southern Research Station

Title: Oligomeric flavanoids. Part 15^a. Base-catalyzed pyran rearrangements of procyanidin B-2, and evidence for the oxidative transformation of B- to A-type procyanidins

Author: Burger, Johann F.W.; Kolodziej, Herbert; Hemingway, Richard W.; Steynberg, Jan P.; Young, Desmond A.; Ferreira, Daneel

Date: 1990

Source: Tetrahedron 46(16):5733-5740

Description: Procyanidin B-2 3 is subject to facile C-ring isomerizations in 0.1M NaHCO₃ solution to form a novel series of 3,4,9,1o-tetrahydro-2H,8H-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).

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Citation

Burger, Johann F.W.; Kolodziej, Herbert; Hemingway, Richard W.; Steynberg, Jan P.; Young, Desmond A.; Ferreira, Daneel  1990.  Oligomeric flavanoids. Part 15^a. Base-catalyzed pyran rearrangements of procyanidin B-2, and evidence for the oxidative transformation of B- to A-type procyanidins.   Tetrahedron 46(16):5733-5740