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An efficient route to a key A-ring synthon for 1α,25-dihydroxyvitamin D3 and its analogs

✍ Scribed by Susumi Hatakeyama; Hiroshi Irie; Takashi Shintani; Yohko Noguchi; Hidetoshi Yamada; Mugio Nishizawa

Publisher
Elsevier Science
Year
1994
Tongue
French
Weight
629 KB
Volume
50
Category
Article
ISSN
0040-4020

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✦ Synopsis

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)-iodoalkeneaskeysteps.

📜 SIMILAR VOLUMES

An efficient enantioselective synthesis
An efficient enantioselective synthesis of 1α,25-dihydroxyvitamin D3 A-ring synthon
✍ Masakazu Koiwa; Georges P.J Hareau; Fumie Sato 📂 Article 📅 2000 🏛 Elsevier Science 🌐 French ⚖ 99 KB

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.