Tandem Allylboration–Prins Reaction for the Rapid Construction of Substituted Tetrahydropyrans: Application to the Total Synthesis of (−)‐Clavosolide A | Zendy

Millán Alba | Zendy; Smith James R. | Zendy; Chen Jack L.Y. | Zendy; Aggarwal Varinder K. | Zendy

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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 , chemistry , yield (engineering) , tandem , moiety , cascade reaction , xylose , sequence (biology) , total synthesis , combinatorial chemistry , organic chemistry , catalysis , materials science , biochemistry , metallurgy , composite material , fermentation

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.

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