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Accepted (AM)Open Access (License Unspecified), Open
Journal article
Transmissive Olefination Route to Putative "Morinol I" Lignans
Journal of organic chemistry, v 77(7), pp 3651-3657
06 Apr 2012
PMCID: PMC3331789
PMID: 22432777
Featured in Collection : UN Sustainable Development Goals @ Drexel
Abstract
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.
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Details
- Title
- Transmissive Olefination Route to Putative "Morinol I" Lignans
- Creators
- Lihua Yao - Duquesne UniversityBhaskar Pitta - Duquesne UniversityP. C. Ravikumar - Duquesne UniversityMatthew Purzycki - Duquesne UniversityFraser 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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- Web of Science research areas
- Chemistry, Organic