A novel glyceryl ester (glyceryl dendryphiellate A), a trinor‐eremophilane (dendryphiellin A1), and eremophilanes (dendryphiellin E1 and E2) from the marine deuteromycete Dendryphiella salina (SUTHERLAND) PUGHet NICOT

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Abstract
Continuing studies of the global extracts from cultures of the marine deuteromycete Dendryphiella salina have led to the isolation of novel compounds that add to the scarce list of marine fungal metabolites. Besides (22E)‐ergosta‐4.6,8(14),22‐tetraen‐3‐one which, though known from basidiomycetes, was unknown in the sea, they are an unusual glyceryl ester, i.e. glycer‐1‐yl dendryphiellale A (= (+)‐(2R)‐2,3‐dihydroxyprop‐l‐yl (6S,2E,4E)6‐methylocta‐2,4‐dienoate; (+)‐1), a trinor‐eremophilane, i.e. dendryphiellin A1 ( = (+)‐(3R*,4E,6E)‐7‐{[(1R*,2S*,7R*,8aR*)‐1,2,6,7,8,8a‐hexahydro‐7‐hydroxy‐1,8a‐dimethyl‐6‐oxonaphthalen‐2yl]oxycarbonyl}‐3‐methylhepta‐4,6‐dienoic acid; (+)‐11), and two eremophilanes, i.e. dendryphiellin El ( = (+)‐(1R*, 2S*, 7S*,8aR*)‐1,2,6,7,8,8a‐hexahydro‐1,8a‐dimethyl‐7‐(1‐methylethenyl)‐6‐oxonaphthalen‐2‐yl(6S,2E,4E)‐6‐methyl‐octa‐2,4‐dienoate; (+)‐13) and dendryphiellin E2 ( = (+)‐(1R*, 2S*, 8aR*)‐1,2,6,7,8,8a‐hexahydro‐7‐isopropyl‐idene‐1,8a‐dimethyl‐6‐oxonaphthalen‐2‐yl (6S,2E,4E)‐6‐Methylocta‐2,4‐dienoate; (+)‐14). Absolute configurations have been established for (+)‐1 via total synthesis and for the acid portion of (+)‐13 and (+)‐14 via transesterification in NaOMe/MeOH which gave in both cases melhyl dendryphiellate A ((+)‐16) of known configuration and the free alcoholic moiety of (+)‐14, i.e. (+)‐17.