P-38 抗マラリア活性を有する海産ジテルペノイド7,20-Diisocyanoadocianeの合成(ポスター発表の部)
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7,20-Diisocyanoadociane is a marine diterpenoid isocyanide isolated from the marine sponge of the genus Adocia collected in Australia, on the Great Barrier Reef. 7,20-Diisocyanoadociane has a unique all-trans-perhydropyrene ring system. 7,20-Diisocyanoadociane strongly inhibits proliferation of the malaria parasite Plasmodium falciparum. The biological activity and unique structural feature prompted the authors to undertake its synthesis. The authors established a formal synthesis of 7,20-diisocyanoadociane using a sequential isomerization-intramolecular Diels-Alder reaction as a key step. The synthesis of 7,20-diisocyanoadociane was conducted starting from known optically active lactone 2 (Scheme 1). Lactone 2 was converted to allylic alcohol 6 by introduction of diene and dienophile moieties. Oxidation of allylic alcohol 6 with IBX resulted, via an intramolecular Diels-Alder reaction, in the spontaneous formation of cis-decalin 8 as the sole product. cis-Decalin 8 was converted to triene 12 by introduction of a diene moiety through a Horner-Wadsworth-Emmons reaction. A solution of triene 12 in mesitylene was heated at 220℃ in the presence of DBU and BHT to facilitate a sequential isomerization-intramolecular Diels-Alder reaction to give a mixture of exo- and endo-cycloadducts 13 (Scheme 2). Following deprotection of the Tr group in 13, the mixture of exo/endo cycloadducts was separated to give alcohols 14a and 14b. Alcohol 14a was converted to diketone 1 via deformylation, reduction of the olefin and isomerization at C-11 and C-15. Diketone 1 was used as Corey's intermediate for the synthesis of 7,20-diisocyanoadociane.
- 天然有機化合物討論会の論文
- 2008-09-01
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- P-38 抗マラリア活性を有する海産ジテルペノイド7,20-Diisocyanoadocianeの合成(ポスター発表の部)