Totalsynthese von (–)‐Norgestrel
- 26 June 1985
- journal article
- research article
- Published by Wiley in Helvetica Chimica Acta
- Vol. 68 (4) , 1054-1068
- https://doi.org/10.1002/hlca.19850680430
Abstract
Total‐Synthesis of (–)‐Norgestrel(–)‐Norgestrel (1a) or (–)‐norethindrone (1b), two active progestational ingredients of currently used contraceptives have been synthesized stereoselectively. Compound 1a has been obtained starting from m‐cresol methyl ether, dimethyl malonate, and (E)‐1,4‐dibromo‐2‐butene. The steroid skeleton has been constructed using an intramolecular Diels‐Alder reaction of an o‐quinodimethane derivative preceeded by a photo‐enolization of an appropriate methyl‐substituted acetophenone derivative. Chirality has been introduced at an early stage during an ScN′ reaction (cf. Scheme 1). Compound 1b has been obtained similarly using a previously reported mixture of the enantiomerically pure constitutional isomers 18b/19b (cf. Scheme 3).This publication has 31 references indexed in Scilit:
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