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Synthesis of Spirolactones from the Limonene System

✍ Scribed by Edyta Paruch; Zbigniew Ciunik; Czesław Wawrzeńczyk

Publisher
John Wiley and Sons
Year
1998
Tongue
English
Weight
263 KB
Volume
1998
Category
Article
ISSN
1434-193X

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✦ Synopsis

Four enantiomeric pairs of spirolactones were obtained in a the syntheses presented. The structures of products were confirmed by X-ray crystallography of 11, 18b, and 19. four step synthesis from (+) and (-) limonene. The Claisen rearrangement and iodolactonization were the key steps of 8a (0.82 g, 2.6 mmol) in dry benzene (3 ml) under N 2 . The mixture (5S,8S)-(Ϫ)-8-(1-Methylethenyl)-1-oxaspiro[4.5]dec-6-en-2one (12b): Obtained (0.27 g, 91%) by the same procedure, from 8b was stirred for 3 d at room temp. and then it was chromatographed (silica gel, hexane/EtOAc, 9:1) to give 0.47 g (95%) of 9; m.p.

(0.5 g, 1.56 mmol); [α] D 24 ϭ Ϫ19.5 (c ϭ 1.1, acetone).

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