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First Total Synthesis of the Sex Pheromone of the Oleander Scale Aspidiotus nerii : An Unusual Sesquiterpenic Functionalized Cyclobutane
Author(s) -
Petschen Inés,
Parrilla Alfredo,
Bosch M. Pilar,
Amela Cristina,
Botar Ana A.,
Camps Francisco,
Guerrero Angel
Publication year - 1999
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/(sici)1521-3765(19991105)5:11<3299::aid-chem3299>3.0.co;2-0
Subject(s) - cyclobutane , steric effects , chemistry , stereochemistry , sex pheromone , ring (chemistry) , natural product , organic chemistry , biology , botany
The rational choice of a hydroxy protecting group , as shown by molecular modeling studies and experimentally confirmed, is a key issue for the success of the first total synthesis of an unusual sesquiterpenic trisubstituted cyclobutane, with a homoprenylated chain on a sterically congested quaternary carbon at the cyclobutane ring. The structure corresponds to the sex pheromone of the oleander scale and is entirely new as a natural product.