The structure of the lichen pigment haemoventosin has been revised to
oxy-3S-methyl-1,6,9-trioxo-1H-naphtho-[2,3-c]pyran (3), mainly on the
basis of long-range delta(C)/delta(H) correlations observed in 2D HMBC
NMR experiments and long-range delta(H)/delta(D) isotope effects obse
rved in partial deuteriation experiments with 10-O-acetylhaemoventosin
; ortho- and para-quinonoid structures were distinguished by means of
the transacetylation inferred in the sodium dithionite reduction of 10
-O-acetylhaemoventosin.