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Total Synthesis of Mycinolide V, the Aglycone of a Macrolide Antibiotic of the Mycinamycin Series
Author(s) -
Ditrich Klaus,
Bube Tomas,
Stürmer Rainer,
Hoffmann Reinhard W.
Publication year - 1986
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.198610281
Subject(s) - aglycone , reagent , chemistry , total synthesis , antibiotics , stereochemistry , macrolide antibiotics , key (lock) , combinatorial chemistry , organic chemistry , computer science , biochemistry , erythromycin , glycoside , computer security
The synthesis of the title compound 1 was accomplished in 29 steps . The C‐1 to C‐10 and C‐11 to C‐17 fragments 2 and 3 , respectively, were prepared separately in enantiomerically pure form and then coupled. A key reagent of the synthesis was the boronate 4 , which can be added highly diastereoselectively to aldehydes.