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Stereoselective Total Synthesis of Mucocin, an Antitumor Agent
Author(s) -
Takahashi Shunya,
Kubota Akemi,
Nakata Tadashi
Publication year - 2002
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/anie.200290038
Subject(s) - desymmetrization , stereoselectivity , chemistry , alkoxy group , alcohol , acrylate , total synthesis , combinatorial chemistry , stereochemistry , organic chemistry , enantioselective synthesis , catalysis , polymer , alkyl , monomer
The THP and THF rings which are regarded as the characteristic structural features of mucocin ( 1 ) were constructed by a SmI 2 ‐induced reductive cyclization of β‐alkoxy acrylate and oxidative cyclization of a homoallyl alcohol, respectively. The key intermediates were synthesized through an efficient desymmetrization of a C 2 ‐symmetric tetraol.