Daphnicyclidins A-H, novel hexa- or pentacyclic alkaloids from two species of Daphniphyllum.
نویسندگان
چکیده
Eight highly modified Daphniphyllum alkaloids with unprecedented fused hexa- or pentacyclic skeletons, daphnicyclidins A-H (1-8), have been isolated from the stems of Daphniphyllum humile and D.teijsmanni, and their structures were elucidated on the basis of spectroscopic data and chemical means. The stereochemistry was elucidated by combination of NOESY correlations, X-ray crystallographic data, and CD analyses.
منابع مشابه
Daphnicyclidins J and K, unique polycyclic alkaloids from Daphniphyllum humile.
Two Daphniphyllum alkaloids with unprecedented polycyclic skeletons, daphnicyclidins J (1) and K (2), have been isolated from the stems of Daphniphyllum humile, and the structures and relative stereochemistry were elucidated on the basis of spectroscopic data. The absolute stereochemistry of 1 was established by chemical correlation with a known-related alkaloid, daphnicyclidin D (3), through a...
متن کاملDaphmanidins C and D, novel pentacyclic alkaloids from Daphniphyllum teijsmanii.
[structure: see text] Two novel alkaloids with an unprecedented fused-pentacyclic skeleton, daphmanidins C (1) and D (2), have been isolated from the leaves of Daphniphyllum teijsmanii, and the structures were elucidated on the basis of spectroscopic data. The relative stereochemistry of 1 and 2 was assigned by combination of NOESY correlations and a simulation analysis. Daphmanidin C (1) eleva...
متن کاملNature knows best: an amazing reaction cascade is uncovered by design and discovery.
The Daphniphyllum alkaloids are a group of highly complex polycyclic alkaloids. Examination of the structures if several members of this family of natural products led to a hypothesis about their mode of biosynthesis (depicted in Scheme I). Based on this hypothetical biosynthetic pathway, a laboratory synthesis was designed that incorporated as a key transformation the novel one-pot transformat...
متن کاملFive new alkaloids from the stem bark of Daphniphyllum macropodum.
Five new alkaloids, daphnicyclidins M and N (compounds 1 and 2) and calyciphyllines Q-S (compounds 3-5), along with four known ones, paxiphylline C (6), macropodumine B (7), macropodumine C (8) and daphnicyclidin A (9) were isolated from the stem bark of Daphniphyllum macropodum. Calyciphylline Q (3) is the first calyciphylline A derivative possessing a double bond between C-18 and C-19. Their ...
متن کاملCalyciphyllines A and B, two novel hexacyclic alkaloids from Daphniphyllum calycinum.
[structure: see text] Two types of Daphniphyllum alkaloids with unprecedented fused-hexacyclic ring systems, calyciphyllines A (1) and B (2), have been isolated from the leaves of Daphniphyllum calycinum (Daphniphyllaceae), and the structures and relative stereochemistry were elucidated on the basis of spectroscopic data.
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
- Journal of the American Chemical Society
دوره 123 46 شماره
صفحات -
تاریخ انتشار 2001