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- W2077500825 abstract "A new approach to the asymmetric synthesis of pentadeca-1,3,5,7,9,11,13,15-octols and their derivatives is presented. It is based on the Sharpless asymmetric dihydroxylation (AD) of 4,4'-methylene[(1R,1'S,6R,6'S)-6-acetoxycyclohept-3-en-1-yl]bis(4-methoxybenzoate) (9), derived from a double [3+4] cycloaddition of the 1,1,3-trichloro-2-oxyallyl cation with 2,2'-methylenedifuran (1). The diol (-)-10, obtained in 98.4% ee from 9 with AD-mix-beta(5x), was oxidised into (2R and 2S,4S,6R)-tetrahydro-2-hydroxy-6-((4S,6S)-(6-hydroxy-4-[(4-methoxybenzoyl)oxy]cyclohept-1-en-1-yl)-2-oxopropyl)-2H-pyran-4-yl 4-methoxybenzoates ((-)-18). By the combinations of Evans' anti and Nasaraka's syn reductions of aldol (-)-18 with the double Mitsunobu reaction, 16 diastereomeric pentadeca-1,3,5,7,9,11,13,15-octols and analogues can be obtained, in principle, with high enantio- and diastereoselectivities." @default.
- W2077500825 created "2016-06-24" @default.
- W2077500825 creator A5082026323 @default.
- W2077500825 creator A5090994439 @default.
- W2077500825 date "2000-11-17" @default.
- W2077500825 modified "2023-10-18" @default.
- W2077500825 title "A New, Non-Iterative Asymmetric Synthesis of Long-Chain 1,3-Polyols" @default.
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- W2077500825 doi "https://doi.org/10.1002/1521-3765(20001117)6:22<4091::aid-chem4091>3.0.co;2-w" @default.
- W2077500825 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/11151841" @default.
- W2077500825 hasPublicationYear "2000" @default.
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