Sato, Manabu published the artcileTotal Synthesis of (-)-Histrionicotoxin through a Stereoselective Radical Translocation-Cyclization Reaction, Recommanded Product: (R)-Oxiran-2-ylmethanol, the publication is Angewandte Chemie, International Edition (2017), 56(4), 1087-1091, database is CAplus and MEDLINE.
Stereoselective total syntheses of (-)-histrionicotoxin and (-)-histrionicotoxin 235A are described. The 1-azaspiro[5.5]undecane skeleton was constructed diastereoselectively by a radical translocation-cyclization reaction involving a chiral cyclic acetal; the use of tris(trimethylsilyl)silane was crucial for the high diastereoselectivity. The cyclization product was converted into (-)-histrionicotoxin 235A through a one-pot partial-reduction-allylation reaction of a derivative containing an unprotected lactam. Finally, two terminal alkenes were transformed into enynes with the 1,3-amino alc. protected as an oxathiazolidine oxide to complete the total synthesis of (-)-histrionicotoxin.
Angewandte Chemie, International Edition published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C3H6O2, Recommanded Product: (R)-Oxiran-2-ylmethanol.
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