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Amino Acids, XIV; (±)‐Pipecolic Acid Derivatives, IV: An Efficient Synthetic Method for the Preparation of (±)‐Baikiain and its Derivatives
Author(s) -
Herdeis Claus,
Engel Wolfram
Publication year - 1993
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.19933260509
Subject(s) - chemistry , regioselectivity , hydroxylation , epoxide , pipecolic acid , hydroxymethyl , piperidine , imine , double bond , hydrolysis , cycloaddition , hydrochloride , hydroboration , dihydroxylation , organic chemistry , geminal , stereochemistry , amino acid , enantioselective synthesis , biochemistry , enzyme , catalysis
[4+2] Cycloaddition of the highly electrophilic imine 2 to 1,3‐butadiene ( 1 ) furnished the Diels‐Alder product 3 . Hydrolysis of the geminal diester provided (±)‐Baikiain hydrochloride ( 4 ). Cis‐Hydroxylation of the double bond of 3 afforded 8 . The trans product 9 was prepared via ring opening of the epoxide 5 . The regioselective hydroboration/oxidation of 3 provided 7 which was oxidized to 11 . Halolactonization of the N ‐tosyl derivative 12 of Baikiain furnished after functional group transformation the 2‐hydroxymethyl‐piperidine‐4‐ol 15 .