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Determination of the absolute configuration of jatamansone (valeranone) by the axial α-haloketone rule

✍ Scribed by Carl Djerassi; T.R. Govindachari; B.R. Pai; K.K. Purushothaman

Book ID
104249752
Publisher
Elsevier Science
Year
1961
Tongue
French
Weight
155 KB
Volume
2
Category
Article
ISSN
0040-4039

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✦ Synopsis

THE skeletal structure 2,3 of jatamansone (identical with valeranone4) is unique among sesquiterpenes. By establishing the location 2b,5 of the carbonyl group, the constitutional problem can be considered to be settled completely in terms of structures I -IV, the only question remaining being the stereochemistry of this sesquiterpene. The degradation 2b of jatamansone to (-)-carvomenthone (V) fixes the absolute configuration of the carbon atom to which t?e isopropyl group is attached, thus leaving the four isomeric repres'antations I -IV open for further consideration. We ' Optical Rotatory Dispersion Studies LII. For preceding paper see C.

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Contribution to the Special Thematic Project ''Advances in Chiroptical Methods'' ## Abstract Cephalochromin, a homodimeric naphthpyranone natural product, contains both axial chirality due to the hindered rotation along the biaryl axis and central chirality due to the C-2, C-2 0 stereogenic cente