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Fe(II)‐Induced Fragmentation Reaction of γ‐Hydroperoxy‐α,β‐enones. Part 1. Synthesis of 13(14→8)‐ abeo ‐Steroids
Author(s) -
Caica† Luigi,
Danieli Bruno,
Lesma Giordano,
Palmisano Giovanni,
Mugnoli Angelo
Publication year - 1987
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.19870700320
Subject(s) - chemistry , fragmentation (computing) , fission , alkylation , tandem , stereochemistry , crystal structure , crystallography , organic chemistry , catalysis , nuclear physics , physics , materials science , composite material , computer science , neutron , operating system
Some steroidal analogues embodying the hitherto unknown 13(14→8)‐ abeo skeleton have been synthesized by Fe(II)‐induced rearrangement (tandem β‐fission/reductive alkylation) of 14α‐hydroperoxy‐7‐en‐6‐ones. The configurational assignment was made by thorough analysis of NMR spectra; the structure of one of the products was unambiguously assessed by X‐ray single‐crystal analysis.