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ChemInform Abstract: Enantiopure Building Blocks for Marine Natural Products via Differentiation of Enantiotopic Groups.

✍ Scribed by W. BEIL; P. G. JONES; F. NERENZ; E. WINTERFELDT

Publisher: John Wiley and Sons
Year: 2010
Weight: 42 KB
Volume: 29
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199840028

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✦ Synopsis

1998 stereochemistry stereochemistry (general, optical resolution) O 0030

40 -028

Enantiopure Building Blocks for Marine Natural Products via Differentiation of Enantiotopic Groups.

-The face-selective cycloaddition of enantiopure cyclopentadiene derivative (II) to the cyclohexadienone (I) furnishes the diastereomerically pure cyclohexenone derivative (III). It is transformed by stereoselective cis-hydroxylation followed by a retro Diels-Alder reaction into title compound (VII), the key intermediate en route to the marine antibiotics agelorin (XIII). Compound (III) is also a valuable intermediate for the preparation of carba-sugar derivatives like (XII). -(BEIL, W.; JONES, P.

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