124512-49-8Relevant academic research and scientific papers
Biosynthetic studies of marine lipids. 24.1 Experimental demonstration of an unprecedented cyclopropane → cyclopropane rearrangement in the biosynthesis of the sponge sterol petrosterol
Doss, George A.,Proudfoot, Johan R.,Silva, J. Cristopher,Djerassi, Carl
, p. 305 - 310 (2007/10/02)
The marine sterol (1) is shown to be biosynthesized From 24-melhylenecholesterol (4) via an unprecedented cyclopropane → cyclopropane rearrangement presumably involving a protonated species of dihydrocalysterol (3). Such rearrangement was confirmed by feeding [28-14C]-24-methylenecholesterol (4) to the sponge Cribrocalina vasculum and demonstrating that the 14C label, originally at C-28 in 4, has migrated to C-24 in 1, Acid-catalyzed cyclopropane ring opening of 1-a key step in the degradation scheme for locating the label-was studied in detail and shown to be accompanied by an unexpected rearrangement process.
