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Biologically active glycosides from asteroidea, XXI. Structure of pectinioside C: Determination of the stereochemistry of the C-17 side chain of the steroidal aglycone

✍ Scribed by Honda, Masanori ;Igarashi, Takashi ;Komori, Tetsuya

Publisher
John Wiley and Sons
Year
1990
Tongue
English
Weight
678 KB
Volume
1990
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

The 3,6‐di‐O‐acetyl derivative 3 of the desulfated aglycone of pectinioside C, (20__S__,24__S__)‐24‐ethylthoransterol A (2), and its 24__R__ and 24__RS__ stereoisomers 4 and 27 have been synthesized stereoselectively from the pregnane derivative 3,6‐di‐O‐acetyl‐asterone (5). Herewith, the stereochemistry at the C‐17 side chain of 2 and of pectinioside C (1) has been determined. (20__S__,24__S__)‐3β‐Acetoxy‐24‐ethyl‐20‐hydroxycholest‐5‐en‐23‐one (18), its 24__R__ and 24__RS__ stereoisomers 21 and 24, respectively, and some steroids with (20__S__)‐20‐hydroxy‐24ζ‐methyl‐26‐homo‐25ζ‐cholestane side chain have also been synthesized.

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