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Evolution of a Synthetic Strategy for the Variecolortides
Author(s) -
Kuttruff Christian A.,
Mayer Peter,
Trauner Dirk
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200712
Subject(s) - chemistry , cycloaddition , block (permutation group theory) , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , geometry , mathematics
The variecolortides are a family of unusual natural products that combine motifs from a variety of biosynthetic streams. Herein, we present the gradual evolution of a convergent synthetic strategy that ultimately culminated in a reaction cascade featuring a hydrogen shift and a cycloaddition followed by a spontaneous air oxidation. Attempts to link an anthrone building block with an exo ‐methylene diketopiperazine using radical chemistry were ultimately unsuccessful, but led to interesting observations that shaped our successful strategy. The total synthesis of variecolortide C is presented for the first time.