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Selective syntheses of leuconolam, leuconoxine, and mersicarpine alkaloids from a common intermediate through regiocontrolled cyclizations by Staudinger reactions†Electronic supplementary information (ESI) available: Experimental details and procedures, compound characterization data, copies of (1)H and (13)C NMR spectra for new compounds. See DOI: 10.1039/c4qo00312hClick here for additional data file.

Li Z, Geng Q, Lv Z, Pritchett BP, Baba K, Numajiri Y, Stoltz BM, Liang G - Org Chem Front (2015)

Bottom Line: Selective syntheses of leuconolam, leuconoxine, and mersicarpine alkaloids bearing distinctive core structures were achieved through Staudinger reactions using a common intermediate.In the key cyclization step, water functioned like a switch to control which core structure to produce.The chemistry allowed for selective syntheses of the group of alkaloids from a simple intermediate through straightforward chemical operations.

View Article: PubMed Central - PubMed

Affiliation: State Key Laboratory and Institute of Elemento-organic Chemistry , Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) , Nankai University , Tianjin 300071 , China . Email: lianggx@nankai.edu.cn.

ABSTRACT

Selective syntheses of leuconolam, leuconoxine, and mersicarpine alkaloids bearing distinctive core structures were achieved through Staudinger reactions using a common intermediate. In the key cyclization step, water functioned like a switch to control which core structure to produce. The chemistry allowed for selective syntheses of the group of alkaloids from a simple intermediate through straightforward chemical operations.

No MeSH data available.


Representative biosynthetically related monoterpene indole alkaloids with distinctive skeleton diversity.
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fig1: Representative biosynthetically related monoterpene indole alkaloids with distinctive skeleton diversity.

Mentions: Leuconolam, leuconoxine, and mersicarpine alkaloids showcase the incredible structural diversity of natural products. These monoterpene indole alkaloid families, though sharing the same biogenetic origin,1 present distinctive skeletons with three completely different polycyclic patterns (1–6, Fig. 1).


Selective syntheses of leuconolam, leuconoxine, and mersicarpine alkaloids from a common intermediate through regiocontrolled cyclizations by Staudinger reactions†Electronic supplementary information (ESI) available: Experimental details and procedures, compound characterization data, copies of (1)H and (13)C NMR spectra for new compounds. See DOI: 10.1039/c4qo00312hClick here for additional data file.

Li Z, Geng Q, Lv Z, Pritchett BP, Baba K, Numajiri Y, Stoltz BM, Liang G - Org Chem Front (2015)

Representative biosynthetically related monoterpene indole alkaloids with distinctive skeleton diversity.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4333676&req=5

fig1: Representative biosynthetically related monoterpene indole alkaloids with distinctive skeleton diversity.
Mentions: Leuconolam, leuconoxine, and mersicarpine alkaloids showcase the incredible structural diversity of natural products. These monoterpene indole alkaloid families, though sharing the same biogenetic origin,1 present distinctive skeletons with three completely different polycyclic patterns (1–6, Fig. 1).

Bottom Line: Selective syntheses of leuconolam, leuconoxine, and mersicarpine alkaloids bearing distinctive core structures were achieved through Staudinger reactions using a common intermediate.In the key cyclization step, water functioned like a switch to control which core structure to produce.The chemistry allowed for selective syntheses of the group of alkaloids from a simple intermediate through straightforward chemical operations.

View Article: PubMed Central - PubMed

Affiliation: State Key Laboratory and Institute of Elemento-organic Chemistry , Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) , Nankai University , Tianjin 300071 , China . Email: lianggx@nankai.edu.cn.

ABSTRACT

Selective syntheses of leuconolam, leuconoxine, and mersicarpine alkaloids bearing distinctive core structures were achieved through Staudinger reactions using a common intermediate. In the key cyclization step, water functioned like a switch to control which core structure to produce. The chemistry allowed for selective syntheses of the group of alkaloids from a simple intermediate through straightforward chemical operations.

No MeSH data available.