Formal Total Synthesis of Brevisamide by Using a Tandem Isomerization/C–O and C–C Bond Formation Reaction | Zendy

Banoth Shivalal | Zendy; Maity Saurabh | Zendy; Kumar Sudheer R. | Zendy; Yadav J. S. | Zendy; Mohapatra Debendra K. | Zendy

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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.

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