Solid Phase Synthesis of Isariin, a Long Chain [beta]-Hydroxy Acid-containing Cyclodepsipeptide, and Its Diastereoisomer

The method of solid phase synthesis was applied to the preparation of isariin (Ia), a β-hydroxydodecanoic acid-containing cyclodepsipeptide metabolite of Isaria cretacea, and its isomer (Ib). The open-chain depsipeptide, H-Val-D-Leu-Ala-Val-DL-Hyd-Gly-OH, was synthesized by coupling successively BOC...

Full description

Saved in:
Bibliographic Details
Published inChemical & pharmaceutical bulletin Vol. 22; no. 9; p. 2136
Main Authors OKADA, KOZO, KUROSAWA, YOTARO, HIRAMOTO, MINORU
Format Journal Article
LanguageEnglish
Published Tokyo Japan Science and Technology Agency 01.09.1974
Online AccessGet full text

Cover

More Information
Summary:The method of solid phase synthesis was applied to the preparation of isariin (Ia), a β-hydroxydodecanoic acid-containing cyclodepsipeptide metabolite of Isaria cretacea, and its isomer (Ib). The open-chain depsipeptide, H-Val-D-Leu-Ala-Val-DL-Hyd-Gly-OH, was synthesized by coupling successively BOC-Val-DL-Hyd-OH, alanine, and Z-Val-D-Leu-OH to resin-bound glycine using dicyclohexylcarbodiimide (DCC) or DCC+hydroxysuccinimide (HOSu) as coupling agent. After cleavage from the resin the depsipeptide was cyclized by means of DCC+HOSu. The cyclization product was successfully resolved, after chromatographic purification on Dowex 50×4 and Sephadex LH-20 column, by preparative thin-layer chromatography on silica gel to afford Ia and Ib in moderate yields.
ISSN:0009-2363
1347-5223