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Synthesis of 7-acetyloxy-3,7-dimethy1-7,8-dihydro-6H-isochromene-6,8-dione and its analogues

✍ Scribed by Tsuneo Suzuki; Kiyoshi Tanemura; Chizuko Okada; The Late Kenichi Arai; Akira Awaji; Takahachi Shimizu; Takaaki Horaguchi

Publisher
Journal of Heterocyclic Chemistry
Year
2001
Tongue
English
Weight
139 KB
Volume
38
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

7‐Alkanoyloxy‐3,7‐dimefhyl‐7,8‐dihydro‐6__H__‐isochromene‐6,8‐diones 12‐15 were synthesized in 69‐16% yields from the reaction of 2,4‐dihydroxy‐3‐methyl‐6‐(2‐oxopropyl)benzaldehyde 11 with p‐toluenesulfonic acid in various carboxylic acids such as acetic acid, propionic acid, butyric acid and heptanoic acid followed by oxidation with lead tetraacetate. On the other hand, (±)‐daldinin A 5 (oleate) was not obtained using oleic acid as a medium. In the cases of heptanoic acid and oleic acid, esters 16 and 17 were produced in 23 and 9% yields, respectively. 6,8‐Dihydroxy‐3,7‐dimethyl‐2‐benzopyrylium p‐toluenesulfonate 31 is considered as the intermediate for the production of 12‐15. Overall yields of isochromenes 12‐15 were 26‐6% starting from 2‐methylresorcinol for seven steps.

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