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Isolation, Structure Determination and Synthesis of New Acetylenic Steroids from the Sponge Calyx nicaaensis

✍ Scribed by Eric Steiner; Carl Djerassi; Ernesto Fattorusso; Silvana Magno; Luciano Mayol; Circo Santacroce; Donato Sica

Publisher: John Wiley and Sons
Year: 1977
Tongue: German
Weight: 563 KB
Volume: 60
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19770600219

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

Two acetylenic steroids, cholest‐5‐en‐23‐yn‐3β‐ol (5) and 26,27‐dinorcholest‐5‐en‐23‐yn‐3β‐ol (3), and another unsaturated steroidalcohol, stigmasta‐5,23‐dien‐3β‐ol (7), were isolated from the sponge Calyx nicaaensis. The structures of these two acetylenic steroids were established by synthesis. Several attempts to synthesize the marine steroids alcohol calysterol (1), with a cyclopropene‐containing side chain, starting from cholest‐5‐en‐23‐yn‐3β‐ol are also recorded. Addition of ethyl‐diazo‐acetate to the triple bond was performed, but the reduction to the methyl derivative yielded decomposition products.

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