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Synthesis of the Right‐Hand Substructure of Solanoeclepin A
Author(s) -
Brière JeanFrançois,
Blaauw Richard H.,
Benningshof Jorg C. J.,
van Ginkel Angeline E.,
van Maarseveen Jan H.,
Hiemstra Henk
Publication year - 2001
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 - 10.1002/1099-0690(200106)2001:12<2371::aid-ejoc2371>3.0.co;2-o
Subject(s) - cyclopropanation , chemistry , cyclopropane , moiety , intramolecular force , cyclobutanone , substructure , stereochemistry , hexane , bicyclic molecule , total synthesis , organic chemistry , ring (chemistry) , catalysis , structural engineering , engineering
A synthesis of the right‐hand substructure 7 of solanoeclepin A ( 1 ), the most active natural hatching agent of potatocyst nematodes, was approached by an intramolecular [2+2] photocycloaddition. The construction of the strained bicyclo[2.1.1]hexane skeleton was achieved in five steps from dioxenone 9 . A Simmons−Smith cyclopropanation enabled the installation of the required cyclopropane. Finally, a TPAP oxidation allowed the smooth formation of the strained cyclobutanone moiety.