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Isolation, Structure Determination and Synthesis of New Acetylenic Steroids from the Sponge Calyx nicaaensis
Author(s) -
Steiner Eric,
Djerassi Carl,
Fattorusso Ernesto,
Magno Silvana,
Mayol Luciano,
Santacroce Circo,
Sica Donato
Publication year - 1977
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19770600219
Subject(s) - chemistry , sponge , cyclopropene , calyx , derivative (finance) , stereochemistry , triple bond , alcohol , double bond , steroid , medicinal chemistry , organic chemistry , biochemistry , hormone , financial economics , economics , botany , biology
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.