Premium
Total Synthesis of (−)‐Salvinorin A
Author(s) -
Line Nathan J.,
Burns Aaron C.,
Butler Sean C.,
Casbohm Jerry,
Forsyth Craig J.
Publication year - 2016
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/chem.201604853
Subject(s) - chemistry , moiety , total synthesis , stereochemistry , furan , stereoselectivity , aldehyde , allylic rearrangement , intramolecular force , diol , ligand (biochemistry) , organic chemistry , receptor , catalysis , biochemistry
Salvinorin A ( 1 ) is natural hallucinogen that binds the human κ‐opioid receptor. A total synthesis has been developed that parlays the stereochemistry of l ‐(+)‐tartaric acid into that of (−)‐ 1 via an unprecedented allylic dithiane intramolecular Diels–Alder reaction to obtain the trans ‐decalin scaffold. Tsuji allylation set the C9 quaternary center and a late‐stage stereoselective chiral ligand‐assisted addition of a 3‐titanium furan upon a C12 aldehyde/C17 methyl ester established the furanyl lactone moiety. The tartrate diol was finally converted into the C1,C2 keto‐acetate.