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Stereoselective Total Synthesis of a Novel D-Homosteroid by a Twofold Heck Reaction

✍ Scribed by Lutz F. Tietze; Sönke Petersen

Publisher
John Wiley and Sons
Year
2000
Tongue
English
Weight
262 KB
Volume
2000
Category
Article
ISSN
1434-193X

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✦ Synopsis

The D-homosteroid 1 was synthesized by two successive Heck reactions starting from enantiopure 3 and the bromoarene 2 containing a (Z)-bromovinyl group. The first intermolecular Pd-catalyzed reaction leads to 6 in a highly regio-and [a]

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✍ Lutz F. Tietze; Sönke Petersen 📂 Article 📅 2001 🏛 John Wiley and Sons 🌐 English ⚖ 337 KB 👁 2 views

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-