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Tandem Allylboration–Prins Reaction for the Rapid Construction of Substituted Tetrahydropyrans: Application to the Total Synthesis of (−)‐Clavosolide A
Author(s) -
Millán Alba,
Smith James R.,
Chen Jack L.Y.,
Aggarwal Varinder K.
Publication year - 2016
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.201511140
Subject(s) - prins reaction , yield (engineering) , tandem , cascade reaction , sequence (biology) , moiety , chemistry , computer science , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , materials science , biochemistry , metallurgy , composite material
Tetrahydropyrans are common motifs in natural products and have now been constructed with high stereocontrol through a three‐component allylboration‐Prins reaction sequence. This methodology has been applied to a concise (13 steps) and efficient (14 % overall yield) synthesis of the macrolide (−)‐clavosolide A. The synthesis also features an early stage glycosidation reaction to introduce the xylose moiety and a lithiation‐borylation reaction to attach the cyclopropyl‐containing side chain.