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Stereoselective Total Syntheses of (+/-)-Isoagatholactone and (+/-)-12α-Hydroxyspongia-13(16),14-diene, Two Marine Sponge Metabolites

DOI: 10.1039/P19830000135

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 135 - 139 (1983)

Update date:2022-08-05

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Authors:

Nakano, TatsuhikoNakano, Tatsuhiko

Hernandez, Maria IsabelHernandez, Maria Isabel

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Article abstract of DOI:10.1039/P19830000135

The highly efficient, stereoselective syntheses of (+/-)-isoagatholactone (1a) and (+/-)-12α-hydroxyspongia-13(16),14-diene (3e), a fundamental skeleton of spongiadiol (3a) and its related furanoid diterpenes, are described. (+/-)-Labda-8(20),13-dien-15-oic acid (6), chosen as the starting material, was cyclised to the known tricyclic compound (2b), which after methylation was subjected to photooxygenation, yielding the allylic alcohol (7a).Refluxing of the alcohol (7a) with 3.5percent sulphuric acid in dioxan afforded the lactone (1b), which after reduction with lithium aluminium hydride led to the diol (2g).Subsequent oxidation of this diol with Collins reagent provided the desired compound (1a).The key precursor for the synthesis of compound (3e) was the allylic alcohol (7a) obtained above.On epoxidation the alcohol (7a) gave the epoxide (13), which by the action with lithium di-isopropylamide led to the α,β-unsaturated γ-lactone (14).Subsequent reduction of this lactone with di-isobutylaluminium hydride afforded the furan (3e).

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