Ascidiatrienolids A-C, novel lactonized eicosanoids from the colonial marine ascidian Didemnum candidum

doi:10.1016/S0040-4039(00)99112-3

Tetrahedron Letters

Volume 30, Issue 21, 1989, Pages 2735-2738

https://doi.org/10.1016/S0040-4039(00)99112-3 Get rights and content

Abstract

Three new eicosanoids (1-3) possessing a unique 9-membered ring lactone and novel sites of oxidation have been isolated from the colonial marine ascidian Didemnum candidum (F. Didemnidae). These compounds further illustrate some intriguing differences in the pathways of eicosanoid production between mammals and several marine invertebrates.

Three new eicosanoids (1–3) possessing a rare 9-membered ring lactone and novel sites of oxidation nave been isolated from the colonial marine ascidian Didemnum candidum.

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Two routes have been explored for the preparation of the title 9 membered lactones. Lactonisation of a hydroxy acid bearing an embryonic unsaturated side chain followed by palladiumcatalysed chain extension was shown to be problematic. The preferred procedure, which involved prior formation of the complete carbon skeleton followed by lactonisation using Mukaiyama conditions, was employed to prepare 8-deoxy-pseudo-Ascidiatrienolide C. The efficiency of the lactonisation process is particularly notable.

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Ascidiatrienolids A-C, novel lactonized eicosanoids from the colonial marine ascidian Didemnum candidum

Abstract

Tetrahedron Lett.