7021. Papuamine

Nomenclature

CAS number: 112455-84-2
(4aS,5aR,10aR,11aS,15aR,15bS,16E,18E,19aS,19bR)-2,3,4,4a,5,5a,6,7,8,9,10,10a,11,11a,12,13,14,15,15a,15b,19a,19b-Docosahydro-1H-diindeno[2,1-f:1′,2′-1][1,5]diazacyclotridecine.
C25H40N2; mol wt 368.60.
C 81.46%, H 10.94%, N 7.60%.

Description and references

Alkaloid originally isolated from Haliclona sp., a marine sponge found in Papua, New Guinea. Exhibits antifungal and antimicrobial activity. Isoln and characterization: B. J. Baker et al., J. Am. Chem. Soc. 110, 965 (1988). Total synthesis: R. M. Borzilleri et al., ibid. 116, 9789 (1994).

Chemical structure

Properties

White solid, mp 167.5-169°. [α]D -150° (c = 1.5 in methanol).

Derivative

Dihydrochloride.

Nomenclature

CAS number: 112347-74-7

Properties

White solid, mp 230° (dec). [α]D -140° (c = 1.3 in CH3OH). uv max (methanol): 241 nm (ε 3000).