Of triquinane terpenes

The capnellenols, e.g. (24) [cf. (10)], are a unique family of sesquiterpenes, found in the soft coral Capnella imbricata. They are related structurally to the hirsutane family of triquinane terpenes, e.g. (18), but with the three methyl groups distributed differently about the tricycle. A special feature of the capnellenols is the presence of an unusual Wj-allylic alcohol functionality associated with ring c. The 8-epimer of (24) has now been synthesized by a route (Scheme 3) in which this novel functionality is introduced by annulation to (23) via reductive cyclization of the keto-acetylene precursor (22), followed by treatment of the resulting allylic alcohol (23) with t-butyl hydroperoxide in the presence of catalytic selenium dioxide. ... 

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See also in sourсe #XX -- [ , , ]

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