Structure and Conformational Analysis of Napelline-Type Diterpenoid Alkaloids View Full Text


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Article Info

DATE

2017-01

AUTHORS

M. N. Sultankhodzhaev, B. Tashkhodzhaev, K. K. Turgunov, U. Kh. Kurbanov, N. I. Mukarramov

ABSTRACT

X-ray crystal structure analyses of six compounds (napelline, napelline N-oxide EtOH solvate, 1-O-benzoylnapelline EtOH solvate, songorine hydrochloride monohydrate EtOH solvate, 1-O-benzoylsongorine, and N-deethylsongorine) showed that the diterpenoid alkaloid napelline had the β-configuration of the C12 hydroxyl. It was found that the N-oxide in napelline N-oxide had the R-configuration. Two types of intramolecular H-bonds could occur in the studied alkaloids and their salts, i.e., between the unshared electron pair on the skeletal N atom and the C1 OH and between the C12 and C15 OH groups. Ring A adopted the boat conformation if the first type of H-bond formed. The second type of H-bond did not cause significant conformational changes. More... »

PAGES

99-104

References to SciGraph publications

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s10600-017-1919-1

DOI

http://dx.doi.org/10.1007/s10600-017-1919-1

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https://app.dimensions.ai/details/publication/pub.1083877014


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