Sintetičke studije za dobijanje (+)-rauvomina B i drugih članova makrolinske/sarpaginske grupe alkaloida
Synthetic studies towards (+)-rauvomine B and other macroline/sarpagine alkaloids
Апстракт
Indole alkaloid (+)-rauvomine B1
contains cyclopropane ring incorporated in the
unprecedented 6/5/6/6/3/5 hexacyclic structure ornate with six stereocenters, making this
compound a challenging synthetic task.
Our strategy for (+)-rauvomine B total synthesis proceeds via a key tetracyclic
intermediate, which could be efficiently prepared from commercially available N-Boc-(S)-
tryptophan in 4 steps: 1) homologization to homotryptophan 2) aldol reaction 3) Pictet Spengler reaction 4) elimination. This efficient route also enabled several other members
of macroline/sarpagine indole alkaloids to be synthesized from this common intermediate,
via unified strategy.
Кључне речи:
total synthesis / macroline/sarpagine / indole alkaloidsИзвор:
58. Savetovanje Srpskog hemijskog društva, Kratki izvodi radova, Beograd 9. i 10. jun 2022. godine, 2022, 58, 134-134Издавач:
- Belgrade : Serbian Chemical Society
Финансирање / пројекти:
- New SMART Synthesis - New Synthetic Methods and their Applications for Rapid Total Syntheses of Complex Natural Products and Bioactive Molecules (RS-ScienceFundRS-Ideje-7750119)
Колекције
Институција/група
Hemijski fakultet / Faculty of ChemistryTY - CONF AU - Đurković, Filip T. AU - Ferjančić, Zorana AU - Bihelović, Filip PY - 2022 UR - http://cherry.chem.bg.ac.rs/handle/123456789/5934 AB - Indole alkaloid (+)-rauvomine B1 contains cyclopropane ring incorporated in the unprecedented 6/5/6/6/3/5 hexacyclic structure ornate with six stereocenters, making this compound a challenging synthetic task. Our strategy for (+)-rauvomine B total synthesis proceeds via a key tetracyclic intermediate, which could be efficiently prepared from commercially available N-Boc-(S)- tryptophan in 4 steps: 1) homologization to homotryptophan 2) aldol reaction 3) Pictet Spengler reaction 4) elimination. This efficient route also enabled several other members of macroline/sarpagine indole alkaloids to be synthesized from this common intermediate, via unified strategy. PB - Belgrade : Serbian Chemical Society C3 - 58. Savetovanje Srpskog hemijskog društva, Kratki izvodi radova, Beograd 9. i 10. jun 2022. godine T1 - Sintetičke studije za dobijanje (+)-rauvomina B i drugih članova makrolinske/sarpaginske grupe alkaloida T1 - Synthetic studies towards (+)-rauvomine B and other macroline/sarpagine alkaloids IS - 58 SP - 134 EP - 134 UR - https://hdl.handle.net/21.15107/rcub_cherry_5934 ER -
@conference{ author = "Đurković, Filip T. and Ferjančić, Zorana and Bihelović, Filip", year = "2022", abstract = "Indole alkaloid (+)-rauvomine B1 contains cyclopropane ring incorporated in the unprecedented 6/5/6/6/3/5 hexacyclic structure ornate with six stereocenters, making this compound a challenging synthetic task. Our strategy for (+)-rauvomine B total synthesis proceeds via a key tetracyclic intermediate, which could be efficiently prepared from commercially available N-Boc-(S)- tryptophan in 4 steps: 1) homologization to homotryptophan 2) aldol reaction 3) Pictet Spengler reaction 4) elimination. This efficient route also enabled several other members of macroline/sarpagine indole alkaloids to be synthesized from this common intermediate, via unified strategy.", publisher = "Belgrade : Serbian Chemical Society", journal = "58. Savetovanje Srpskog hemijskog društva, Kratki izvodi radova, Beograd 9. i 10. jun 2022. godine", title = "Sintetičke studije za dobijanje (+)-rauvomina B i drugih članova makrolinske/sarpaginske grupe alkaloida, Synthetic studies towards (+)-rauvomine B and other macroline/sarpagine alkaloids", number = "58", pages = "134-134", url = "https://hdl.handle.net/21.15107/rcub_cherry_5934" }
Đurković, F. T., Ferjančić, Z.,& Bihelović, F.. (2022). Sintetičke studije za dobijanje (+)-rauvomina B i drugih članova makrolinske/sarpaginske grupe alkaloida. in 58. Savetovanje Srpskog hemijskog društva, Kratki izvodi radova, Beograd 9. i 10. jun 2022. godine Belgrade : Serbian Chemical Society.(58), 134-134. https://hdl.handle.net/21.15107/rcub_cherry_5934
Đurković FT, Ferjančić Z, Bihelović F. Sintetičke studije za dobijanje (+)-rauvomina B i drugih članova makrolinske/sarpaginske grupe alkaloida. in 58. Savetovanje Srpskog hemijskog društva, Kratki izvodi radova, Beograd 9. i 10. jun 2022. godine. 2022;(58):134-134. https://hdl.handle.net/21.15107/rcub_cherry_5934 .
Đurković, Filip T., Ferjančić, Zorana, Bihelović, Filip, "Sintetičke studije za dobijanje (+)-rauvomina B i drugih članova makrolinske/sarpaginske grupe alkaloida" in 58. Savetovanje Srpskog hemijskog društva, Kratki izvodi radova, Beograd 9. i 10. jun 2022. godine, no. 58 (2022):134-134, https://hdl.handle.net/21.15107/rcub_cherry_5934 .