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Short, Convergent Synthesis of Locked Retinals
Author(s) -
Andrä Michal S.,
Tzschucke C. Christoph
Publication year - 2014
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.201403006
Subject(s) - chemistry , wittig reaction , context (archaeology) , ylide , optogenetics , retinal , convergent synthesis , combinatorial chemistry , stereochemistry , neuroscience , paleontology , biochemistry , biology
We report a short and convenient synthesis of two configurationally locked retinals that are important for applications in the context of optogenetics. The C11–C15 cyclopentyl fragments of both retinals were obtained by palladium‐catalysed alkoxycarbonylation and merged with the rest of the carbon skeleton through Wittig olefination. The preparation of the required and known ylide precursor was revisited and optimised. This synthetic route enables gram‐scale preparation of both retinal derivatives.