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Stereoselective Convergent Synthesis of 24,25‐Dihydroxyvitamin D 3 Metabolites: A Practical Approach
Author(s) -
Pérez Sestelo José,
Cornella Iván,
de Uña Olga,
Mouriño Antonio,
Sarandeses Luis A.
Publication year - 2002
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20020617)8:12<2747::aid-chem2747>3.0.co;2-j
Subject(s) - stereoselectivity , conjugate , stereocenter , chemistry , iodide , aqueous solution , yield (engineering) , zinc , vitamin , stereochemistry , combinatorial chemistry , organic chemistry , enantioselective synthesis , biochemistry , catalysis , mathematics , materials science , mathematical analysis , metallurgy
Vitamin D 3 active metabolites 24 R ,25‐(OH) 2 ‐D 3 , 24 S ,25‐(OH) 2 ‐D 3 , and 1 α ,24 R ,25‐(OH) 3 ‐D 3 were synthesized by a convergent and stereoselective approach. In the synthetic route, the stereogenic center at C‐24 was generated through ultrasonically induced aqueous conjugate addition of iodide 6 to Seebach's dioxolanone 5 , and the vitamin D triene system was constructed using the Lythgoe approach. The synthesis, which is both short (seven steps from iodide 6 ) and efficient (32–40 % overall yield), allows the preparation of large quantities of the metabolites and provides a novel example of a highly stereoselective reaction promoted by the zinc‐copper couple in aqueous media.