Premium
Photochemical Synthesis of an L ‐Erythrose Building Block and Its use in the Preparation of Methyl 2,3, O ‐Isopropylidene‐β‐ L ‐apio‐ L ‐furanoside
Author(s) -
Nehrings Alfred,
Scharf HansDieter,
Runsink Jan
Publication year - 1985
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198508771
Subject(s) - cycloaddition , block (permutation group theory) , chemistry , stereochemistry , combinatorial chemistry , medicinal chemistry , catalysis , organic chemistry , combinatorics , mathematics
The synthesis of branched carbohydrates , e.g., the title compound 2 , from nonsugar building blocks is achieved by a chirally controlled photoaldol reaction. [2+2] Cycloaddition of (−)‐8‐phenylmenthyl phenylglyoxylate PhCOCO 2 R * to 2,2‐dimethyl‐1,3‐dioxole leads in exo fashion diastereoselectively to 1 , one of four possible oxetanes; 1 is then converted in several steps into 2 .