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Tandem Prins Cyclization for the Stereoselective Synthesis of Bridged Benzopyran Derivatives
Author(s) -
Subba Reddy Basi V.,
Srivastava Nikhil,
Begum Zubeda,
Lakshmi Jerripothula K.,
Sridhar Balasubramanian
Publication year - 2016
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201600196
Subject(s) - chemistry , stereoselectivity , tandem , prins reaction , tricyclic , benzopyran , stereochemistry , cascade reaction , combinatorial chemistry , phenol , organic chemistry , catalysis , materials science , composite material
A tandem bicyclization strategy has been developed for the stereoselective synthesis of 3,4‐dihydro‐2 H ,6 H ‐2,6‐methanobenzo[ b ][1,5]dioxocine derivatives in good yields and selectivities through the cyclocondensation of 2‐(1‐hydroxy‐3‐methylbut‐3‐en‐1‐yl)phenol with various aldehydes by using 10 mol % BF 3 ⋅ OEt 2 . This is the first reported stereoselective construction of a bridged tricyclic skeleton through a cascade Prins cyclization procedure. This process constitutes an elegant strategy for the quick construction of tricyclic architectures in a single step.
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