Diplodia pinea

The diplodialides are a family of ten-membered ring macrocyclic lactones isolated from the pathogenic fungus Diplodia pinea. Structural studies by Wada in 1976 had shown these compounds to be quite similar to recifeiolide (1), with an additional oxygen functionality included p to the lactone carbonyl. Diplodialides A, B, C, and D (47-50) are the four most common members of this group. 

The biosynthetic reduction of the polyketide chain may prevent the formation of aromatic products. Instead, several lactones are formed. For example, a series of bio-active pentaketide metabolites containing a ten-membered ring have been isolated. These include the diplodialides e.g. diplodialide A, 4.73) from Diplodia pinea, the pyrenolides e.g. pyrenolide A, 4.74) from Pyrenophora teres and the cephalosporolides e.g. cephalosporolide B, 4.75) from Cephalosporium aphidi-cola. An unusual dimeric pentaketide, thiobiscephalosporolide A (in which the two lactones are held together by a sulfur), has also been obtained from... 

EE-Protected D-lactaldehyde 954 is an efficient chiral source for the asymmetric center of (+ )-diplodialide A (960), a metabolite isolated from the culture filtrate of the plant pathogenic fUngus Diplodia pinea [253] (Scheme 130). The carbon skeleton is assembled through two olefination reactions, the first a Wittig reaction of 954 with phosphorane 955 to give the Z... 

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