‘Upenamide: An Unprecedented Macrocyclic Alkaloid from the Indonesian SpongeEchinochalinasp.
- 17 November 2000
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 65 (25) , 8465-8469
- https://doi.org/10.1021/jo000789w
Abstract
‘Upenamide (1) represents a new class of macrocyclic marine alkaloid possessing both spirooxaquinolizidinone and hemiaminal ring systems. It was isolated from the Indonesian sponge Echinochalina sp. The gross structure of 1 was elucidated by spectroscopic methods and accurate mass measurements. A suggestion is made as to its biogenetic origin.Keywords
This publication has 30 references indexed in Scilit:
- Kauluamine, an unprecedented manzamine dimer from an Indonesian marine sponge, Prianos sp.Journal of the American Chemical Society, 1995
- 2-Alkoxy-3-oxoalkyl-tetrahydropyrans and -tetrahydrofurans: versatile intermediates in heterocyclic synthesisJournal of the Chemical Society, Perkin Transactions 1, 1995
- Arenastatin A, a potent cytotoxic depsipeptide from the Okinawan marine sponge Dysidea arenariaTetrahedron Letters, 1994
- Study of 1,2-chlorine migration in (.alpha.,.alpha.-dichlorobenzyl)chlorocarbene generated by laser flash photolysis of 3-chloro-3-(.alpha.,.alpha.-dichlorobenzyl)diazirineThe Journal of Organic Chemistry, 1992
- High-field FT NMR application of Mosher's method. The absolute configurations of marine terpenoidsJournal of the American Chemical Society, 1991
- Araguspongines B, C, D, E, F, G, H, and J, new vasodilative bis-1-oxaquinolizidine alkaloids from an Okinawan marine sponge, Xestospongia sp.CHEMICAL & PHARMACEUTICAL BULLETIN, 1989
- Stereospecific replacement of sulfur from chiral .gamma.-(arylsulfanyl)butyrolactones. Synthesis of optically pure ring-fused .gamma.-butyrolactonesJournal of the American Chemical Society, 1988
- Intramolecular electrostatic stabilization of an SN1 transition stateThe Journal of Organic Chemistry, 1973
- The Nuclear Magnetic Resonance Spectra of the Angular Proton in Benzo[a]- and Indolo[a]quinolizidinesJournal of the American Chemical Society, 1964
- Insect Sex Attractants. I. The Isolation, Identification, and Synthesis of the Sex Attractant of the Gypsy Moth1Journal of the American Chemical Society, 1961