A series of morinol-type lignans were rapidly assembled using a Grignard-based transmissive olefination. In combination with palladium-catalyzed arylations, the strategy provides stereoselective access to (7Z,7'E), (7E,7'E), and (7E,7'Z) morinol diastereomers and the (7Z,8'E) and (7E,8'E) conjugated analogues. Critical for the E/Z stereoselectivity is a new, general method for converting alkenenitriles to alkenemethanols that circumvents the enal E/Z isomerization commonly encountered during conventional i-Bu2AlH reduction.
Transmissive Olefination Route to Putative "Morinol I" Lignans
Creators
Lihua Yao - Duquesne University
Bhaskar Pitta - Duquesne University
P. C. Ravikumar - Duquesne University
Matthew Purzycki - Duquesne University
Fraser F. Fleming - Duquesne University
Publication Details
Journal of organic chemistry, v 77(7), pp 3651-3657
Publisher
American Chemical Society; Washington, DC
Number of pages
7
Grant note
2R15AI051352-03 / National Institutes of Health; United States Department of Health & Human Services; National Institutes of Health (NIH) - USA
R15AI051352 / NATIONAL INSTITUTE OF ALLERGY AND INFECTIOUS DISEASES; United States Department of Health & Human Services; National Institutes of Health (NIH) - USA; NIH National Institute of Allergy & Infectious Diseases (NIAID)
Resource Type
Journal article
Language
English
Academic Unit
Chemistry
Web of Science ID
WOS:000302388000075
Scopus ID
2-s2.0-84859565529
Other Identifier
991020898496604721
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