Refereed journal article or data article (A1)
Biomimetic Total Synthesis of Angiopterlactone B and Other Potential Natural Products
List of Authors: Kotammagari TK, Gonnade RG, Bhattacharya AK
Publisher: AMER CHEMICAL SOC
Publication year: 2017
Journal: Organic Letters
Journal name in source: ORGANIC LETTERS
Journal acronym: ORG LETT
Volume number: 19
Issue number: 13
Start page: 3564
End page: 3567
Number of pages: 4
ISSN: 1523-7060
DOI: http://dx.doi.org/10.1021/acs.orglett.7b01525
Abstract
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.
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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