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Methyl α-acyloxy-γ-methylene-β-tetronate. Preparation and use as a building block for the synthesis of the spirotetronic acid structure of chlorothricolide

✍ Scribed by Kaoru Okumura; Kousuke Okazaki; Kei Takeda; Eiichi Yoshii

Publisher: Elsevier Science
Year: 1989
Tongue: French
Weight: 272 KB
Volume: 30
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)99656-4

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✦ Synopsis

The Diels-Alder reaction of the title compound 4 and octatrienol 10, which were prepared from 44methoxy-5-methylene-2(5H)-furanone and furfuryl alcohol or D-glyceraldehyde, respectively, produced in high yield a mixture of stereo-and regio-isomeric spirotetronates: 14, X5, and 16 in about 65:25:10 ratio. The exe-mode adduct 15 (R= 2,4_difluorophenyl) was transformed into carboxylic acid 19, the tetronic acid subunit of chlorothricolide (l), and also to 21 which can be utilized in the synthesis of 1. Chlorithricolide (l), the aglycone of the antibiotic chlorothricin reported in 1969,l has been the molecule of synthetic endeavors in several laboratories. 2*3 Of the two

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