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BIBTEX RIS

Synthesis of Enantiomerically Pure Heterosteroids by Intramolecular Hetero‐Diels‐Alder Reaction

1990; Wiley; Volume: 29; Issue: 5 Linguagem: Inglês

10.1002/anie.199005271

ISSN

1521-3773

Autores

Lutz F. Tietze, Uwe Beifuß, Magdolna Lőkös, Matthias Rischer, Axel Göhrt, G. M. SCHELDRICK,

Tópico(s)

Oxidative Organic Chemistry Reactions

Resumo

A tandem Knoevenagel/hetero-Diels–Alder reaction of the aldehyde 2 with the cyclic 1,3-dioxo compound 1 and its analogues leads stereoselectively to the trans-bonded heterosteroids 3 (de > 98%). Aldehyde 2 is obtained by ozonolysis of enantiomerically pure tetrahydroindanone derivatives, which are in turn readily available by the Wiechert-Hajos procedure.

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