A1 Vertaisarvioitu alkuperäisartikkeli tieteellisessä lehdessä

Biomimetic Total Synthesis of Angiopterlactone B and Other Potential Natural Products




TekijätKotammagari TK, Gonnade RG, Bhattacharya AK

KustantajaAMER CHEMICAL SOC

Julkaisuvuosi2017

JournalOrganic Letters

Tietokannassa oleva lehden nimiORGANIC LETTERS

Lehden akronyymiORG LETT

Vuosikerta19

Numero13

Aloitussivu3564

Lopetussivu3567

Sivujen määrä4

ISSN1523-7060

DOIhttps://doi.org/10.1021/acs.orglett.7b01525


Tiivistelmä
A one-pot biomimetic synthesis of (-)-angiopterlactone B and its enantiomer (+)-angiopterlactone B has been accomplished via TBAF-catalyzed tandem ring contraction followed by oxa-Michael/Michael addition sequence. Comparison of specific optical rotations, absolute configurations, and CD spectra of natural, synthesized (-)-angiopterlactone B and (+)-angiopterlactone B unequivocally proves that the isolated angiopterlactone B must be levorotatory. Synthesis of hitherto undiscovered natural products 18 and 20 and analogues of angiopterlactone B demonstrate the versatility of this method.



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