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Enantioselective total synthesis of all of the known chiral cleroindicins (C-F): clarification among optical rotations and assignments.

ABSTRACT: Enantioselective syntheses of all of the named chiral members of the cleroindicin family (C-F) are reported. This effort demonstrates the synthetic utility of a 2,4-dihydroxybenzaldehyde as a starting material for natural product synthesis through the use sequential o-quinone methide chemistry and diastereoselective dearomatization. Natural cleroindicin F was shown to be nearly racemic, and an optically pure synthetic sample of cleroindicin F was found to racemize under slightly basic conditions. All other natural chiral cleroindicins are shown to be partially racemic.

SUBMITTER: Wenderski TA

PROVIDER: S-EPMC3063707 | biostudies-literature | 2009 Jun

REPOSITORIES: biostudies-literature

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Enantioselective total synthesis of all of the known chiral cleroindicins (C-F): clarification among optical rotations and assignments.

Wenderski Todd A TA Huang Shenlin S Pettus Thomas R R TR

The Journal of organic chemistry 20090601 11

Enantioselective syntheses of all of the named chiral members of the cleroindicin family (C-F) are reported. This effort demonstrates the synthetic utility of a 2,4-dihydroxybenzaldehyde as a starting material for natural product synthesis through the use sequential o-quinone methide chemistry and diastereoselective dearomatization. Natural cleroindicin F was shown to be nearly racemic, and an optically pure synthetic sample of cleroindicin F was found to racemize under slightly basic conditions ...[more]

PMID: 19476394

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