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Regiospecific syntheses of dl-phyllostine and dl-epoxydon (phyllosinol)

โœ Scribed by Akitami Ichihara; Kengo Oda; Sadao Sakamura

Book ID
104237005
Publisher
Elsevier Science
Year
1972
Tongue
French
Weight
197 KB
Volume
13
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Previously we reported a synthesis of 3 dl-phyllostine 1 and conversion of epoxydonl) 1 (phyllosino13)) t o other minor constituents isolated from culture broth of phyllosticta sp 4) . In this communication we would like to describe regiospecific syntheses of dl-phyllostine 1 and dl-epoxydon 9 (phyllosinol), both of which are physiollogically active compounds among highly oxygenated cyclohexane derivatives occurred naturally 5) . 0 0 HOCb 0 :::o HOC? " v,,, 0 ,,I*0 0 %H 1 2 2-Hydroxymethyl-1,4-benzoquinone 2 prepared from gentisyl alcohol 6) was treated with dihydropyrane and p-toluenesulfonic acid in anhydrous ether to give quantitatively pyranylated compound 2 , m.p. 69.4d71.1ยฐC7), ClzH/+O+, ir ).

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