Biomimetic Total Synthesis of Angiopterlactone B and Other Potential Natural Products



: Kotammagari TK, Gonnade RG, Bhattacharya AK

Publisher: AMER CHEMICAL SOC

: 2017

: Organic Letters

: ORGANIC LETTERS

: ORG LETT

: 19

: 13

: 3564

: 3567

: 4

: 1523-7060

DOI: https://doi.org/10.1021/acs.orglett.7b01525


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.



Last updated on 2024-26-11 at 17:48