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- W2074302235 endingPage "4558" @default.
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- W2074302235 abstract "An enantiodivergent strategy for the total chemical synthesis of both naturally occurring (+)-fomannosin (1) and its (−)-antipode (ent-1) from α-d-glucose has been developed and successfully implemented. The key steps in the overall pathway include the following: (i) application of the zirconocene-mediated ring contraction of vinyl furanosides for the construction of highly substituted cyclobutanols; (ii) the use of ring-closing metathesis to form the pendant five-membered ring; (iii) making recourse to a monothio malonic ester to allow for chemoselective reduction to sensitive lactone intermediate 45; (iv) hydroxyl-directed dihydroxylation with OsO4 to generate 48; and (v) sequential elimination via a cyclic sulfite and a cyclobutyl triflate. The bridge between the enantiomeric series consisted of a six-step linkup involving the structural modification of 22 so as to generate ent-30b. Optical activity was fully preserved throughout." @default.
- W2074302235 created "2016-06-24" @default.
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- W2074302235 date "2008-05-20" @default.
- W2074302235 modified "2023-10-16" @default.
- W2074302235 title "The Carbohydrate−Sesquiterpene Interface. Directed Synthetic Routes to Both (+)- and (−)-Fomannosin from <scp>d</scp>-Glucose" @default.
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- W2074302235 doi "https://doi.org/10.1021/jo8004233" @default.
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