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Biomimetic Total Synthesis of Angiopterlactone B and Other Potential Natural Products
Julkaisun tekijät: Kotammagari TK, Gonnade RG, Bhattacharya AK
Kustantaja: AMER CHEMICAL SOC
Julkaisuvuosi: 2017
Journal: Organic Letters
Tietokannassa oleva lehden nimi: ORGANIC LETTERS
Lehden akronyymi: ORG LETT
Volyymi: 19
Julkaisunumero: 13
Aloitussivu: 3564
Lopetussivun numero: 3567
Sivujen määrä: 4
ISSN: 1523-7060
DOI: http://dx.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.
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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