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Protecting‐Group‐Free Total Syntheses of Rubrolide R and S
Author(s) -
Schacht Mathias,
Boehlich Gordon Jacob,
de Vries Jessica,
Bertram Stephanie,
Gabriel Gülsah,
Zimmermann Phyllis,
Heisig Peter,
Schützenmeister Nina
Publication year - 2017
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.201700158
Subject(s) - chemistry , aldol reaction , total synthesis , protecting group , aldol condensation , virus , stereochemistry , organic chemistry , catalysis , virology , alkyl , biology
The two marine natural products rubrolide R ( 1 ) and S ( 2 ) were synthesised in only three linear steps starting from commercially available tetronic acid without using protecting‐group chemistry. Key steps in the syntheses were the Pd‐catalysed Suzuki–Miyaura cross‐coupling followed by a vinylogous aldol condensation. Both compounds have been tested for their antibiotic and antiviral activities. At a concentration of 10 µ m rubrolide R ( 1 ) and S ( 2 ), a 2‐log and 1.5‐log reduction in virus titre has been detected for a seasonal influenza virus (H3N2) and the pandemic swine influenza virus (pH1N1), respectively.