The structure of delavayine — An alkaloid from Stephania delovayi

The genus Stephania (Menispermaceae): Chemical and pharmacological perspectives

“…Stephodeline (Il'inskaya et al, 1973), 16-oxodelavayine (Il'inskaya et al, 1972), delavayine (25) (Fadeeva et al, 1971a) and isostephodeline (Perel'son et al, 1975).…”

Substrate-Modified Functional Group Reactivity: Hasubanan and Acutumine Alkaloid Syntheses

“…Semihydrogenation of 12 – 14 (Crabtree’s catalyst) , provided the key cis -alkenes 15 – 17 , which underwent acid-mediated cyclization to form the tetracycles 18 , 20 , and 21 , respectively. A two-step sequence comprising debromination and hydrogenation transformed 18 to (−)-hasubanonine ( 19 ). , Hydrogenation of 20 and 21 (Wilkinson’s catalyst) provided (−)-runanine ( 30 ) and (−)-delavayine ( 31 ), − respectively. Hasubanan alkaloids of varying oxidation states were then accessed from the tetracycle 21 .…”

Developments in the Synthesis of Hasubanan Alkaloids

“…[19] Geography of their distribution is mostly covered by tropical regions, although the northernmost species were grown on the Caucasian coast of Black Sea region. [20,21] Pharmacological properties of these plants, including properties of the individual chemical constituents, and timeline of the discovery have been covered in a comprehensive reviews in 2010 [19] and 2022. [22] This review is focused exclusively on chemical synthesis of the hasubanan derivatives.…”

“…Generally, hasubanans are produced by the plants of Stephania genus of the family Menispermaceae [19] . Geography of their distribution is mostly covered by tropical regions, although the northernmost species were grown on the Caucasian coast of Black Sea region [20,21] . Pharmacological properties of these plants, including properties of the individual chemical constituents, and timeline of the discovery have been covered in a comprehensive reviews in 2010 [19] and 2022 [22]…”