𝔖 Bobbio Scriptorium
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Biomimetic synthesis of a preclavulone a model

✍ Scribed by E.J. Corey; Kurt Ritter; Miguel Yus; Carmen Nájera

Book ID
104227251
Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
278 KB
Volume
28
Category
Article
ISSN
0040-4039

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✦ Synopsis

A synthetic route to the preclavulone-A (3) analogs 11 and 14 via allene oxide and 2-oxidopentadienyl cation intermediates is described which is based on the proposed biosynthesis of 3.

Clavuluriu viridis, a Pacific coral which produces the clavulone family of prostanoids (e.g. clavulone I (l)), converts arachidonic acid to the probable clavulone precursor preclavulone A (PC-A, 3)' by way of 8-(R)-HPETE (Q2 It has been proposed that the biosynthesis of 3 from 2 parallels that for the plant regulator cisjasmonic acid,3 and proceeds via allene oxide and oxidopentadienyl cation intermediates as outlined in Chart I.

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