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Asymmetric total synthesis of an A-ring precursor to hormonally active 1.alpha.,25-dihydroxyvitamin D3

โœ Scribed by Posner, Gary H.; Kinter, Chris M.


Book ID
126435413
Publisher
American Chemical Society
Year
1990
Tongue
English
Weight
393 KB
Volume
55
Category
Article
ISSN
0022-3263

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๐Ÿ“œ SIMILAR VOLUMES


Asymmetric synthesis of 1ฮฑ,25-dihydroxyv
โœ Georges P.J Hareau; Masakazu Koiwa; Fumie Sato ๐Ÿ“‚ Article ๐Ÿ“… 2000 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 113 KB

The A-ring precursor of 1ฮฑ,25-dihydroxyvitamin D 3 [(E)-4] has been prepared starting from the (5S)-tertbutyldimethylsiloxy-2-cyclohexenone [(S)-1] via eight steps in 19% overall yield, where a catalytic osmium dihydroxylation which sets the stereochemistry of the hydroxyl group at C 1 and a regiose

An efficient enantioselective synthesis
โœ Masakazu Koiwa; Georges P.J Hareau; Fumie Sato ๐Ÿ“‚ Article ๐Ÿ“… 2000 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 99 KB

The asymmetric synthesis of the A-ring of 1ฮฑ,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.