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Intramolecular, Reductive Coupling of Bis‐α,β‐unsaturated Ketones
Author(s) -
Wenkert Ernest,
Moeller Peter D. R.
Publication year - 1989
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.198900021
Subject(s) - chemistry , cyclopropane , intramolecular force , ketone , tricyclic , lithium (medication) , ammonia , total synthesis , medicinal chemistry , birch reduction , stereochemistry , organic chemistry , ring (chemistry) , medicine , endocrinology
Abstract The reduction‐rearrangement chemistry of two rigidly held doubly vinylogous β‐diketones has been investigated. One hydrophenanthrene dienedione was a tricyclic intermediate in the Wilds total steroid synthesis and the other was prepared from the Wieland‐Miescher ketone. Lithium‐ammonia reduction yielded a cyclopropanedione and a cyclopropanoketol, respectively. Treatment of these compounds with acid furnished cyclopropane‐cleaved ketoenones.