Abstract
Conformational aspects of the 1-oxaquinolizidine ring system found in the xestospongin/araguspongine family of natural products has been studied by molecular modeling and NMR spectroscopy. Stereochemical complexities [e.g., (i) cis- vs trans-decalin-like conformers and (ii) relative configuration of variously substituted 1-oxaquinolizidines] associated with this bridgehead nitrogen-containing skeleton are discussed. Experimental equilibrium values are rationalized. Reassignment of the stereostructures for araguspongines B (from 4 to 6) and E (from 5 to 2) is made in light of the above.
Original language | English (US) |
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Pages (from-to) | 6904-6910 |
Number of pages | 7 |
Journal | Journal of Organic Chemistry |
Volume | 59 |
Issue number | 23 |
DOIs | |
State | Published - Nov 1 1994 |