Journal
SYNLETT
Volume 31, Issue 16, Pages 1581-1586Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0040-1707201
Keywords
total synthesis; Stemonaalkaloids; cyclic stereocontrol; Mukaiyama-Michael reaction; DFT calculation
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Funding
- Academy of Finland [259532, 297874, 307624]
- NKFIH Hungary [K-112028]
- Academy of Finland (AKA) [259532, 307624, 297874, 307624, 297874, 259532] Funding Source: Academy of Finland (AKA)
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Total syntheses of stemoamide, 9a-epi-stemoamide, and 9a,10-epi-stemoamide by a convergent A + B ring-forming strategy is reported. The synthesis required a diastereoselective late-stage methylation of the ABC stemoamide core that successfully enabled access to three of the four possible diastereomeric structures. For the natural stemoamide series, the diastereoselectivity can be rationalized both by kinetic and thermodynamic arguments, whereas for the natural 9a-epi-stemoamide series, the kinetic selectivity is explained by the prepyramidalization of the relevant enolate.
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