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Formal Total Synthesis of Brevisamide by Using a Tandem Isomerization/C–O and C–C Bond Formation Reaction
Author(s) -
Banoth Shivalal,
Maity Saurabh,
Kumar Sudheer R.,
Yadav J. S.,
Mohapatra Debendra K.
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600142
Subject(s) - chemistry , isomerization , tandem , aldol reaction , stereoselectivity , cascade reaction , stereochemistry , total synthesis , dihydropyran , medicinal chemistry , organic chemistry , catalysis , materials science , composite material
A highly stereoselective formal total synthesis of brevisamide is described that proceeds through a convergent pathway and utilizes our own tandem isomerization/C–O and C–C bond formation reaction as the key step to construct the trans ‐2,6‐disubstituted dihydropyran ring system. Other significant reactions in this synthesis include an iodolactonization, a Crimmins‐modified “non‐Evans” syn aldol reaction, and a Horner–Wadsworth–Emmons olefination.