Chasmanine intermediate, C₂₄H₃₅NO₆

Abstract

Abstract. Monoclinic, P2t/a, This study has confirmed that the synthetic procedure has successfully produced the required chasmanine intermediate.

The addition of 2,4-dinitrobenzenesulphenyl chloride to 2-methylenebicyclo[2.2.1]hept-5-ene: the crystal structure of 1-chloromethyl-3-endo-(2′,4′-dinitrophenylthio)tricyclo[2.2.1.02,6]heptane, C14H13ClN2O4S

“…is observed. Similar effects were found in, for example, ergotamine (21,22) in a chain of 5 atoms in which the end oxygens were an acceptor and a donor in hydrogen bond formation. The shortening of C(12)-C(13) is significant and reflects similar alternate changes in electron distribution through the N(15)-C(12) -C(13)-C (14) -N(18) chain.…”

Chasmaconitine 0.5-Methanol Solvate

“…The six-membered tings A (C1-C5, Cll) and E (C4, C5, C11, C17, N1, C19) adopt chair conformations. Ring A is slightly flattened at C1 due to the methoxy substituent attached to C 1, as observed in the structures of a chasmanine intermediate (Przybylska & Ahmed, 1980) and aconitine (Codding, 1982). Ring E is also slightly flattened at C 19 due to the presence of an ethyl substituted N atom in the ring.…”

“…The C14 atom is 0.708 (5),~ out of the plane of the remaining four atoms of the ring which are essentially planar; maximum deviation 0.022 (2),~. The C17 atom is 0.734 (4),~ out of the plane formed by the remaining atoms of ring F. The benzoate moiety attached to C14 is almost planar, with 08 lying 0.173 (7)A below and 09 0.087 (7) (Przybylska & Ahmed, 1980), aconitine (Codding, 1982) and delfinifoline (Kerr & Codding, 1982), which bear the basic skeleton of (1), have been reported previously.…”

Pseudaconitine

“…The six-membered rings A (C1-C5 and C 1 l) and E (C4, C5, Cll, C17, N1 and C19) adopt chair conformations. These rings are slightly flattened, as observed in the structures of a chasmanine intermediate (Przybylska & Ahmed, 1980), aconitine (Codding, 1982), chasmanthinine (Parvez et al, 1998a), chasmaconitine methanol solvate (Parvez et al, 1998), 14-o-benzoyl-8-ethoxyand 14-o-benzoyl-8-methoxy-bikhaconines (Parvez et at., 1998b and 3o~-bikhaconine acetone solvate (Parvez et al, 1998c). The six-membered ring D (C8, C9 and C13-C16) has a half-chair conformation, with C14 0.895 (4) ,A, out of the plane of the remaining ring atoms [maximum deviation 0.070 (2),A,].…”