Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Studies on Terpenoids and Related Alicyclic Compounds. XVI. Total Syntheses of Furanosesquiterpenes ; (±)-Furanoeremophilane, (±)-Furanoligularane, (±)-9, 10-Dehydrofuranoeremophilane, (±)-3β-Hydroxyfuranoeremophilane, and (±)-3β-Furanoligularanol
山川 浩司佐藤 毅
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キーワード: reductive dehydroxylation
ジャーナル フリー

1978 年 26 巻 12 号 p. 3704-3714

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Total syntheses of (±)-furanoeremophilane (34), (±)-furanoligularane (37), (±)-9, 10-dehydrofuranoeremophilane (32), (±)-ligularone (1), (±)-3β-hydroxyfuranoeremophilane (25), and (±)-3β-furanoligularanol (31) are described. Reduction of cis-annulated 6, 9-dioxo-3-ketal (9) with NaBH4 gave ketols (10a and 11a). 11a was desketalized and subjected to selective reduction with P-I2 to give 3, 6-diketone (13), which was already converted into (±)-1. Reduction of 3, 9-dioxo-6α-ol (14), derived from 10a, with P-I2 afforded a mixture of 17-20. Both 3, 9-diketones (18 and 19) were converted into 3, 9-diol acetates (24b and 30b), respectively. The Birch reductions were effected for deacetoxylation of α'-acetoxy-α-substituted furan, e.g. (26) and the results are shown in Table I. Reductive deacetoxylation of 24b and 30b by the Birch procedure gave (±)-25 and (±)-31, respectively. (±)-Hydroxyfuranoeremophilane (6), derived from 18, was treated with POCL3-pyridine to give (±)-32. Reductive deacetoxylation of acetate (33) by the Birch procedure gave (±)-34. trans-Annulated 3, 9-diketone (19) was derived to the acetate (36b), which was converted by the Birch procedure into (±)-37.

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