10-Hydroxy Lycopodium alkaloids: Difference between revisions
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[[File:10-Hydroxylycopodine, Deacetylpaniculine and Paniculine.jpeg|center|400px]] |
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The first [[enantioselective synthesis]] of 10-hydroxylycopodine, deacetylpaniculine and paniculine was published by Mrinmoy Saha and [[Rich Carter]] in 2013. Two key ring-closure steps were accomplished by an [[organocatalysis|organocatalytic]] [[Michael reaction]] and a [[Lewis acid]]-catalyzed [[Mannich reaction]].<ref name= Lycopodines >{{cite journal |last1=Saha |first1=Mrinmoy |first2= Rich G. |last2= Carter |title=Toward a Unified Approach for the Lycopodines: Synthesis of 10-Hydroxylycopodine, Deacetylpaniculine, and Paniculine |journal=Organic Letters |date=February 2013|volume=15 |issue=4 |pages=736–739 |doi=10.1021/ol303272w |pmid=23384410 |pmc=3616490}}</ref> The impact of the C10 stereochemistry on the Michael addition to construct the C7–C12 bond and on the Mannich cyclization have been explored recently. <ref name= 10-Hydroxy Lycopodium alkaloids >{{cite journal |last1=Saha |first1=Mrinmoy |first2= Xin |last2= Li | |
The first [[enantioselective synthesis]] of 10-hydroxylycopodine, deacetylpaniculine and paniculine was published by Mrinmoy Saha and [[Rich Carter]] in 2013. Two key ring-closure steps were accomplished by an [[organocatalysis|organocatalytic]] [[Michael reaction]] and a [[Lewis acid]]-catalyzed [[Mannich reaction]].<ref name= Lycopodines >{{cite journal |last1=Saha |first1=Mrinmoy |first2= Rich G. |last2= Carter |title=Toward a Unified Approach for the Lycopodines: Synthesis of 10-Hydroxylycopodine, Deacetylpaniculine, and Paniculine |journal=Organic Letters |date=February 2013|volume=15 |issue=4 |pages=736–739 |doi=10.1021/ol303272w |pmid=23384410 |pmc=3616490}}</ref> The impact of the C10 stereochemistry on the Michael addition to construct the C7–C12 bond and on the Mannich cyclization have been explored recently. <ref name= 10-Hydroxy Lycopodium alkaloids >{{cite journal |last1=Saha |first1=Mrinmoy |first2= Xin |last2= Li |first3= Nathan D. |last3= Collett |first4= Rich G. |last4= Carter |title=Unified Synthesis of 10-Oxygenated Lycopodium Alkaloids: Impact of C10-Stereochemistry on Reactivity |journal=Organic Letters |date=June 2016|volume=81 |issue=14 |pages=5963−5980 |doi=10.1021/acs.joc.6b00900</ref> |
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==See also== |
==See also== |
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Revision as of 18:51, 4 August 2016
The 10-hydroxy Lycopodium alkaloids, 10-hydroxylycopodine, deacetylpaniculine and paniculine, are a series of natural products isolated from a Chilean club moss Lycopodium confertum. Deacetylpaniculine and paniculine were also isolated from Lycopodium paniculatum.[1]
The Lycopodium alkaloids are of interest due to their biological activity and unique skeletal characteristics,[2] however, many compounds in this class have not been well studied.
Synthesis
The first enantioselective synthesis of 10-hydroxylycopodine, deacetylpaniculine and paniculine was published by Mrinmoy Saha and Rich Carter in 2013. Two key ring-closure steps were accomplished by an organocatalytic Michael reaction and a Lewis acid-catalyzed Mannich reaction.[3] The impact of the C10 stereochemistry on the Michael addition to construct the C7–C12 bond and on the Mannich cyclization have been explored recently. Cite error: The <ref> tag has too many names (see the help page).
See also
References
- ^ Muñoz, Orlando M.; Castillo, M.; San Feliciano, A. (January 1990). "High Resolution NMR Studies of Paniculine and Related Lycopodium Compounds". Journal of Natural Products. 53 (1): 200–203. doi:10.1021/np50067a032.
- ^ "Lycopodine and the Lycopodium Alkaloids" (PDF).
- ^ Saha, Mrinmoy; Carter, Rich G. (February 2013). "Toward a Unified Approach for the Lycopodines: Synthesis of 10-Hydroxylycopodine, Deacetylpaniculine, and Paniculine". Organic Letters. 15 (4): 736–739. doi:10.1021/ol303272w. PMC 3616490. PMID 23384410.