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ChemInform Abstract: Biomimetic Synthesis of (-)-Xestospongin A (IX), (+)-Xestospongin C (VIII), (+)-Araguspongine B (VII) and the Correction of Their Absolute Configurations.

✍ Scribed by J. E. BALDWIN; A. MELMAN; V. LEE; C. R. FIRKIN; R. C. WHITEHEAD


Publisher
John Wiley and Sons
Year
2010
Weight
34 KB
Volume
30
Category
Article
ISSN
0931-7597

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✦ Synopsis


Biomimetic Synthesis of (-)-Xestospongin A (IX), (+)-Xestospongin C (VIII), (+)-Araguspongine B (VII) and the Correction of Their Absolute Configurations.

-Key steps in the synthesis of title compounds (VII)-(IX) are stereoselective formation of the hydroxy ester (III), dimerization of the pyridine (IV), intramolecular ring closure yielding the bis-oxaquinolizidine (VI), and reduction of (VI).The results unambiguously establish that the natural compounds are the enantiomers in all three cases.

-(BALDWIN,