In:
Bioscience, Biotechnology, and Biochemistry, Informa UK Limited, Vol. 84, No. 7 ( 2020-07-02), p. 1339-1344
Abstract:
Catathelasmols C, D, and E, which had been isolated from Catathelasma imperiale as inhibitors for 11-hydroxysteroid dehydrogenases, were comprehensively semisynthesized from commercially available D-glutamic acid. The key synthetic intermediate, (R)-pentane-1,2,5-triol, was site-selectively acetylated by treatment with vinyl acetate and Candida antarctica lipase B (Novozym 435) in tetrahydrofuran (THF) at 25°C to furnish 1,5-diacetate (catathelasmol E, quantitative). The acetylation occurred site-selectively on the primary alcohols at the C-1 and C-5 positions over the secondary alcohol at the C-2 position. Dichromic acid oxidation provided 2-oxopentane-1,5-diyl diacetate (catathelasmol C, 78%). Burkholderia cepacia lipase-catalyzed transesterification with methanol in THF at – 5°C proceeded preferentially on the acetate at C-1 located adjacent to the C-2 carbonyl group over the other terminal acetate at the C-5 position. 5-Hydroxy-4-oxopentyl acetate (catathelasmol D) was obtained in 53% yield.
Type of Medium:
Online Resource
ISSN:
0916-8451
,
1347-6947
DOI:
10.1080/09168451.2020.1754159
Language:
English
Publisher:
Informa UK Limited
Publication Date:
2020
detail.hit.zdb_id:
2110940-0
detail.hit.zdb_id:
1106450-X
SSG:
12
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