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Regio‐ and Enantioselective Prenyl Anion Transfer: Application to the Total Synthesis of (−)‐Rosiridol
Author(s) -
Hong BorCherng,
Hong JangHsing,
Tsai YannChien
Publication year - 1998
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19980302)37:4<468::aid-anie468>3.0.co;2-z
Subject(s) - enantioselective synthesis , chemistry , prenylation , aldehyde , natural product , total synthesis , stereochemistry , absolute configuration , retrosynthetic analysis , monoterpene , organic chemistry , catalysis , enzyme
At elevated temperature (refluxing THF) prenyl anion adds regio‐ and enantioselectively to aldehyde 1 when a chiral, borneol‐derived ligand is present. This reaction is the key stepin the first total synthesis of the monoterpene (−)‐rosiridol (retrosynthesis is shown on the right). In addition, the absolute configuration of this natural product has been assigned conclusively. M=Zn, R= t BuMe 2 Si.