2016
DOI: 10.1007/s11418-016-1012-2
|View full text |Cite
|
Sign up to set email alerts
|

Synthesis and stereochemical determination of an antiparasitic pseudo-aminal type monoterpene indole alkaloid

Abstract: 5-Nor stemmadenine alkaloids, isolated from the genus Tabernaemontana, display a range of bioactivity. 16-Hydroxy-16,22-dihydroapparicine, the active component of an extract from the Tabernaemontana sp. (dichotoma, elegans, and divaricate), exhibited potent antimalarial activity, representing the first such report of the antimalarial property of 5-nor stemmadenine alkaloids. We, therefore, decided to attempt the total synthesis of the compound to explore its antimalarial activity and investigate structure and … Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
1

Citation Types

0
2
0

Year Published

2019
2019
2024
2024

Publication Types

Select...
4
1

Relationship

0
5

Authors

Journals

citations
Cited by 5 publications
(2 citation statements)
references
References 107 publications
0
2
0
Order By: Relevance
“…Glycosidation with 7‐nitroindole and continuous Pd/C reduction and Boc protection gave 7‐aminoindolyl C ‐glycoside 14 . The final full deprotection by acid treatment yielded 15 without the decomposition of the C ‐glycoside moiety, despite the presence of an acid‐sensitive vinylogous aminal moiety (pseudo‐aminal) [9] . From these results, it can be deduced that our synthetic method of C ‐azanucleosides worked well, because highly stereocontrolled reactions did not require a complicated isomer separating process and mild reaction conditions avoided any decomposition or epimerization of the benzylic C ‐glycosidic bond.…”
Section: Resultsmentioning
confidence: 77%
“…Glycosidation with 7‐nitroindole and continuous Pd/C reduction and Boc protection gave 7‐aminoindolyl C ‐glycoside 14 . The final full deprotection by acid treatment yielded 15 without the decomposition of the C ‐glycoside moiety, despite the presence of an acid‐sensitive vinylogous aminal moiety (pseudo‐aminal) [9] . From these results, it can be deduced that our synthetic method of C ‐azanucleosides worked well, because highly stereocontrolled reactions did not require a complicated isomer separating process and mild reaction conditions avoided any decomposition or epimerization of the benzylic C ‐glycosidic bond.…”
Section: Resultsmentioning
confidence: 77%
“…Conolidine ( 2 ), a 5-nor-stemmadenine-type alkaloid (Figure ), was isolated from the stem bark of Tabernaemontana divaricata by Kam and co-workers in 2004 . This alkaloid possesses a strained 1-azabicyclo[4.2.2]­decane framework with an E -exocyclic trisubstituted double bond.…”
mentioning
confidence: 99%