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An efficient enantioselective synthesis of 1α,25-dihydroxyvitamin D3 A-ring synthon

✍ Scribed by Masakazu Koiwa; Georges P.J Hareau; Fumie Sato

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
99 KB
Volume
41
Category
Article
ISSN
0040-4039

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✦ Synopsis

The asymmetric synthesis of the A-ring of 1α,25-dihydroxyvitamin D 3 , (Z)-2, from 5-tert-butyldimethylsiloxy-2-cyclohexenone [(S)-1], is described where an intramolecular lactonization using cat. scandium triflate is the key reaction.

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An efficient route to a key A-ring synth
An efficient route to a key A-ring synthon for 1α,25-dihydroxyvitamin D3 and its analogs
✍ Susumi Hatakeyama; Hiroshi Irie; Takashi Shintani; Yohko Noguchi; Hidetoshi Yama 📂 Article 📅 1994 🏛 Elsevier Science 🌐 French ⚖ 629 KB

An efficient and highly stereoselective route to the Roche's A-ring synthon of la.25 dihydroxyvitamin 4 from R-(-)-epichlorohydrin has been developed utilizing double propargylatioa of R-(-)-epichlorohydrin and palladium(O) catalyzed intramolecular Heck type of reactiOn of the o-vinyl-(Z)-iodoalkene