Total synthesis of everninomicin 13,384-1 - Part 3: Synthesis of the DE fragment and completion of the total synthesis

Authors
Nicolaou, KC Mitchell, HJ Rodriguez, RM Fylaktakidou, KC Suzuki, H Conley, SR
Citation
Kc. Nicolaou et al., Total synthesis of everninomicin 13,384-1 - Part 3: Synthesis of the DE fragment and completion of the total synthesis, CHEM-EUR J, 6(17), 2000, pp. 3149-3165
Citations number
19
Categorie Soggetti
Chemistry
Journal title
CHEMISTRY-A EUROPEAN JOURNAL
ISSN journal
09476539 → ACNP
Volume
6
Issue
17
Year of publication
2000
Pages
3149 - 3165
Database
ISI
SICI code
0947-6539(20000901)6:17<3149:TSOE1->2.0.ZU;2-U
Abstract
The stereoselective construction of the DE fragment (2) of everninomicin 13 ,384-1 (1) is reported. From the two possible ways of inserting the DE frag ment between the A(1)B(A)C and FGHA(2) domains of the natural product, the sequence involving the DEFGHA(2) segment was found to be the most viable. T his coupling was followed by attachment of a suitably protected and activat ed A(1)B(A)C fragment which led, after orthoester construction and final de protection to the targeted everninomicin 13,384-1 (1), completing the total synthesis of this complex naturally occurring substance.