Asymmetric Total Synthesis of (−)-Erogorgiaene and Its C-11 Epimer and Investigation of Their Antimycobacterial Activity

A short, nine‐step, highly enantioselective synthesis of (−)‐erogorgiaene and its C‐11 epimer is reported. The key stereochemistry controlling steps involve catalytic asymmetric crotylation, anionic oxy‐Cope rearrangement and cationic cyclisation. (−)‐Erogorgiaene exhibited promising antitubercular...

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Veröffentlicht in:	Chemistry : a European journal 2016-09, Vol.22 (40), p.14390-14396
Hauptverfasser:	Incerti-Pradillos, Celia A., Kabeshov, Mikhail A., O'Hora, Paul S., Shipilovskikh, Sergei A., Rubtsov, Aleksandr E., Drobkova, Vera A., Balandina, Svetlana Yu, Malkov, Andrei V.
Format:	Artikel
Sprache:	eng
Schlagworte:	allylation Antitubercular Agents - chemical synthesis Antitubercular Agents - chemistry Antitubercular Agents - pharmacology asymmetric catalysis Asymmetry Catalysis Catalysts Cationic Cations Chemistry Chemistry Techniques, Synthetic - methods Diterpenes - chemical synthesis Diterpenes - chemistry Diterpenes - pharmacology Enantiomers enantioselectivity Humans Multidrug resistance Mycobacterium tuberculosis - drug effects rearrangement Stereochemistry Stereoisomerism Synthesis total synthesis Tuberculosis Tuberculosis - drug therapy
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Zusammenfassung:	A short, nine‐step, highly enantioselective synthesis of (−)‐erogorgiaene and its C‐11 epimer is reported. The key stereochemistry controlling steps involve catalytic asymmetric crotylation, anionic oxy‐Cope rearrangement and cationic cyclisation. (−)‐Erogorgiaene exhibited promising antitubercular activity against multidrug‐resistant strains of Mycobacterium tuberculosis. Up to the nines: A short, nine‐step, highly enantioselective synthesis of (−)‐erogorgiaene and its C‐11 epimer is reported (see scheme). The key stereochemistry controlling steps involve catalytic asymmetric crotylation, anionic oxy‐Cope rearrangement and cationic cyclisation. (−)‐Erogorgiaene exhibited promising antitubercular activity against multidrug‐resistant strains of Mycobacterium tuberculosis.
ISSN:	0947-6539 1521-3765
DOI:	10.1002/chem.201602440