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Synthesis of New, Unnatural Macrocyclic Trichothecenes: 3‐isoverrucarin A ((1″‐ O )(3→4) abeo ‐verrucarin A), verrucinol, and verrucene. 46th Communication on verrucarins and roridins
Author(s) -
Jeker Nicolas,
Tamm Christoph
Publication year - 1988
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.19880710808
Subject(s) - chemistry , moiety , stereochemistry , deoxygenation , residue (chemistry) , ring (chemistry) , trichothecene , organic chemistry , mycotoxin , catalysis , food science
A new unnatural macrocyclic trichothecene, an analogue of verrucarine A ( 1 ), which was named 3‐Isoverrucarin A ((1″‐ O )(3→4) abeo ‐verrucarin A; 3 ) was synthesized starting from anguidine ( 5 ). The two key reactions were the removal of the 4β‐acetoxy group of anguidine ( 5 ) by a Barton deoxygenation and the final macrolactonization. During the cyclization procedure, two unexpected new macrocyclic by‐products, which were named verrucinol ( 19 ) and verrucene ( 20 ), were formed. They represent novel types of macrocyclic trichothecenes, the macrolidic moiety of verrucene ( 20 ) consisting only of the ( Z,E )‐muconic‐acid residue. The formation of the analogous macrolide 26 of verrucene ( 20 ) was not possible, probably because the ring strain is too strong.