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Enantioselective synthesis of (+)-estrone exploiting a hydrogen bond-promoted Diels-Alder reaction.

ABSTRACT: Starting from Dane's diene and methylcyclopentenedione, (+)-estrone is synthesized along the Quinkert-Dane route in 24% total yield. The key step is an enantioselective Diels-Alder reaction promoted by an amidinium catalyst as efficiently as by a traditional Ti-TADDOLate Lewis acid.

SUBMITTER: Weimar M

PROVIDER: S-EPMC2852147 | biostudies-literature | 2010 Apr

REPOSITORIES: biostudies-literature

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Enantioselective synthesis of (+)-estrone exploiting a hydrogen bond-promoted Diels-Alder reaction.

Weimar Marko M Dürner Gerd G Bats Jan W JW Göbel Michael W MW

The Journal of organic chemistry 20100401 8

Starting from Dane's diene and methylcyclopentenedione, (+)-estrone is synthesized along the Quinkert-Dane route in 24% total yield. The key step is an enantioselective Diels-Alder reaction promoted by an amidinium catalyst as efficiently as by a traditional Ti-TADDOLate Lewis acid. ...[more]

PMID: 20302330

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