ChemInform Abstract: Stereoselective Synthesis of Steroids by Heck Reaction.
β Scribed by L. F. TIETZE; T. NOEBEL; M. SPESCHA
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 27 KB
- Volume
- 28
- Category
- Article
- ISSN
- 0931-7597
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β¦ Synopsis
Stereoselective Synthesis of Steroids by Heck Reaction.
-A new strategy based on the synthesis of the B-ring of the steroid structure is described by a double Heck reaction between the halogen ethenyl benzenes (I) and the indene derivative (II). The formation of the compounds (IV) can also be carried out without isolation of (III). The hitherto unknown estrone derivatives (IV) can be used as starting materials for further novel steroids. Moreover, a variety of compounds can be synthesized by variation of (I) and (II) since the novel Pdcatalyzed anellation of (II) provides a general access to steroidal systems. -
π SIMILAR VOLUMES
The estrane 4 was synthesized by two successive Heck reactions starting from enantiopure 2 and the cyclohexenone 5, which contains a (Z)-bromovinyl group. The first intermolecular Pd-catalyzed reaction leads to 10 in a highly regioand diastereoselective manner. Transformation of the enone [a] Georg-
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