ISSN:
0899-0042
Keywords:
cyclotriveratrylene
;
cyclotriphenolene
;
cryptophane
;
thiovanillin
;
resolution
;
enantiomers
;
diastereoisomers
;
circular dichroism
;
exciton chirality
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
A new route to (+)-(M) and (-)-(P)-cyclotriphenolene (1) is described, starting from 4-mercapto-3-methoxybenzaldehyde (thiovanillin (7)), which was converted into rac-3-methoxy-4-[(1-carboxyethyl)thio]benzyl alcohol (9). The latter was resolved by crystallization of its cinchonidine salts to give (-)-9, to which (S) absolute configuration was assigned. On reaction with formic acid, (-)-(S)-9 afforded the C3-cyclotiveratrylene diastereomers (-)-(P)-11a and (-)-(M)-11b which were separated and submitted to Raney Ni desulfuration to give the (+) and (-)-cyclotrianisylene enantiomers (4), which in turn were converted to (+) and (-)-1 on demethylation. Finally, (-)-1 was transformed into (+)-cryptophane-C according to a previously described method. Chirality 9:446-453, 1997. © 1997 Wiley-Liss, Inc.
Additional Material:
10 Ill.
Type of Medium:
Electronic Resource
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