Total synthesis of astrosterioside A, an anti-inflammatory asterosaponin
Y Dai, B Yu - Chemical Communications, 2015 - pubs.rsc.org
Y Dai, B Yu
Chemical Communications, 2015•pubs.rsc.org… Herein we report the first total synthesis of astrosterioside A (1). … In summary, we have
accomplished the first total synthesis of astrosterioside A (1), a characteristic
asterosaponins with potent anti-inflammatory activities, with a convergent linear sequence
of 24 steps and in a high 6.8% overall yield. The synthesis features stereoselective HWE
olefination to construct the steroidal 20(22)E-ene-23-one side chain (11+14→15),
regioselective glycosylation of the xylopyranoside 4-OH (8+9→18), and highly efficient gold(I)-catalyzed …
accomplished the first total synthesis of astrosterioside A (1), a characteristic
asterosaponins with potent anti-inflammatory activities, with a convergent linear sequence
of 24 steps and in a high 6.8% overall yield. The synthesis features stereoselective HWE
olefination to construct the steroidal 20(22)E-ene-23-one side chain (11+14→15),
regioselective glycosylation of the xylopyranoside 4-OH (8+9→18), and highly efficient gold(I)-catalyzed …
Astrosterioside A, a sulfated steroidal hexasaccharide isolated from starfish Astropecten monacanthus showing potent anti-inflammatory activity, was synthesized in a convergent linear sequence of 24 steps and in 6.8% overall yield from adrenosterone.
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