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 activity against multidrug-resistant strains of Mycobacterium tuberculosis. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Authors
Incerti-Pradillos C.A.1 , Kabeshov M.A.1 , O'Hora P.S.1 , Shipilovskikh S.A.1, 2 , Rubtsov A.E.2 , Drobkova V.A.2 , Balandina S.Y.2 , Malkov A.V. 1, 3
Journal
Chemistry - A European Journal
Publisher
Wiley-VCH Verlag
Number of issue
40
Language
English
Pages
14390-14396
Status
Published
Link
External link
DOI
10.1002/chem.201602440
Volume
22
Year
2016
Organizations
  • 1 Department of Chemistry, Loughborough University, Loughborough, LE11 3TU, United Kingdom
  • 2 Department of Chemistry, Perm State University, Bukireva 15, Perm, 614990, Russian Federation
  • 3 Chemistry Department, Peoples' Friendship University of Russia, Miklukho-Maklaya 6, Moscow, 117198, Russian Federation
Keywords
allylation; asymmetric catalysis; enantioselectivity; rearrangement; total synthesis
Date of creation
19.10.2018
Date of change
19.10.2018
Short link
https://repository.rudn.ru/en/records/article/record/4360/
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