Cembrane and pseudopterane diterpenoids of the octocoral Pseudopterogorgia acerosa

The Journal of Organic Chemistry
1991.0

Abstract

The diterpenoid metabolites isolated from Pseudopterogorgia acerosa collected off the coast of Tobago have been investigated. Collections made in the month of March showed a different distribution of these metabolites from a collection made in July. The dominant constituents in March were acidic diterpenoids which were converted by reaction with diazomethane to deoxypseudopterolide (1), a pseudopterane, and acerosolide (2), a cembrane. Esters 1 and 2 were isolated directly from the July collection, which also afforded the novel nitrogenous pseudopteranoid tobagolide (3). Tobagolide undergoes a novel reaction with acetic anhydride that leads to the displacement of Me₂N by OAc. Tobagolide reacts with diazomethane to form a pyrazoline. Structural assignments have depended heavily on 2-D NMR spectroscopy; in particular, the value of our FLOCK pulse sequence for establishing two-bond and three-bond ¹³C-¹H shift correlations is illustrated.

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