Organic Letters
Organic Letters
5 years ago

Biomimetic Total Synthesis of Angiopterlactone B and Other Potential Natural Products

Biomimetic Total Synthesis of Angiopterlactone B and Other Potential Natural Products
Tharun K. Kotammagari, Rajesh G. Gonnade, Asish K. Bhattacharya
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01525

DOI: 10.1021/acs.orglett.7b01525

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