Total Synthesis of Laingolide B Stereoisomers and Assignment of Absolute Configuration.
Org Lett
; 20(11): 3358-3361, 2018 06 01.
Article
em En
| MEDLINE
| ID: mdl-29781266
ABSTRACT
Total synthesis of (-)-(2 R,9 S)- and (+)-(2 S,9 S)-stereoisomers of laingolide B has been accomplished by using sequential ring-closing metathesis (RCM) and alkene isomerization to construct the macrocyclic trans- N-methyl enamide moiety. The Myers alkylation was used to secure the C2 stereochemistry of the two RCM precursors from a common (9 S)-C3-C9 alkyl iodide. The absolute configuration of laingolide B has been assigned as (2 S,9 R) by comparison of the optical rotation data.
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01-internacional
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MEDLINE
Idioma:
En
Revista:
Org Lett
Ano de publicação:
2018
Tipo de documento:
Article