Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 39, Pages 11812-11815Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201706046
Keywords
asymmetric synthesis; domino reactions; organocatalysis; steroids; total synthesis
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Funding
- JSPS KAKENHI [JP16H01128]
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Enantioselective total synthesis of estradiol methyl ether has been accomplished in a pot-economical manner using five reaction vessels and four purifications. The key reaction is a diphenylprolinol silyl ether mediated domino Michael/aldol reaction to afford bicyclo[4.3.0]nonane derivatives, containing the A, C, and D rings of steroids, as a single isomer with excellent enantioselectivity. Six reactions such as oxidation, hydrogenation, formation of acid chloride, Friedel-Crafts reaction, deprotection, and reduction can be carried out in the last one-pot sequence.
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