Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 24, Pages 13204-13219Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b02293
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Funding
- JSPS KAKENHI [JP16K13082, JP16H01126, JP25282228]
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Polycavernosides A and B are glycosidic macrolide natural products isolated as the toxins causing fatal human poisoning by the edible red alga Gracilaria edulis (Polycavernosa tsudai). Total synthesis of polycavernosides A and B has been achieved via a convergent approach. The synthesis of the macrolactone core structure is highlighted by the catalytic asymmetric syntheses of the two key fragments using hetero-Diels-Alder reaction and Kiyooka aldol reaction as the key steps, their union through Suzuki-Miyaura coupling, and Keck macrolactonization. Finally, glycosylation with the L-fucosyl-D-xylose unit and construction of the polyene side chain through Stifle coupling completed the total synthesis of polycavernosides A and B.
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