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1 article(s) from Strnad, Miroslav

Synthesis of ergostane-type brassinosteroids with modifications in ring A

Vladimir N. Zhabinskii,
Darya A. Osiyuk,
Yuri V. Ermolovich,
Natalia M. Chaschina,
Tatsiana S. Dalidovich,
Miroslav Strnad and
Vladimir A. Khripach

Beilstein J. Org. Chem. 2017, 13, 2326–2331, doi:10.3762/bjoc.13.229

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Graphical Abstract

Scheme 1: Structural features of epicastasterone (1), epibrassinolide (2) and A-ring units 3–12 of BS biosynt...

Jump to Scheme 1

Scheme 2: (a) Ac₂O, Py, DMAP, 60 ^°C; (b) K₂CO₃, MeOH, 20 °C (97% over 2 steps); (c) TCDI, DMAP, THF, 65 °C (7...

Jump to Scheme 2

Scheme 3: (a) MsCl, Py, 20 °C (95%); (b) Zn, NaI, DMF, 150 °C (83%); (c) KOH, MeOH, 65 °C (96%).

Jump to Scheme 3

Scheme 4: (a) MCPBA, CH₂Cl₂, 20 °C (90%); (b) NBS, DME, 20 °C; (c) KOH, MeOH, 20 °C (85% over 2 steps).

Jump to Scheme 4

Scheme 5: (a) BnBr, DMAP, Bu₂SnO, TBAI, DIPEA, 110 °C (94%); (b) PCC, CH₂Cl₂, 20 °C (84%); (c) H₂, Pd/C, 20 °...

Jump to Scheme 5

Scheme 6: (a) TsCl, DMAP, Py, 30 °C (91%); (b) Py, 115 °C (65%); (c) KOH, MeOH, 20 °C (52%).

Jump to Scheme 6

Scheme 7: (a) NaBH₄, EtOH, −25 °C (49%); (b) KOH, MeOH, 65 °C (85%).

Jump to Scheme 7

Scheme 8: (a) Anisaldehyde, TMSCl, MeOH, 20 °C; (b) BnBr, DMAP, Bu₂SnO, TBAI, DIPEA, 110 °C (86% over 2 steps...

Jump to Scheme 8

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Published 02 Nov 2017

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