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First Total Synthesis of (+)‐Membrine
Author(s) -
Wirth Thomas
Publication year - 1997
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199719970616
Subject(s) - chemistry , diselenide , electrophile , selenium , diphenyl diselenide , nucleophile , optically active , total synthesis , intramolecular force , combinatorial chemistry , sequence (biology) , nucleophilic addition , organic chemistry , catalysis , biochemistry
The easily accessible, optically active diselenide 1 is converted into the chiral selenium electrophile 2 and used for oxyselenenylation reactions of alkenes with functionalized nucleophiles. This reaction allows the synthesis of addition products 4, 6 and 10 with the selenium functionality as precursors for an intramolecular radical cyclization. This strategy is applied to the first total synthesis of optically pure (+)‐membrine ( 13 ) by a short synthetic sequence.