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Simple, stereocontrolled synthesis of thromboxane B2 from D-glucose

✍ Scribed by E.J. Corey; Masakatsu Shibasaki; Jochen Knolle

Book ID
104244347
Publisher
Elsevier Science
Year
1977
Tongue
French
Weight
159 KB
Volume
18
Category
Article
ISSN
0040-4039

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✦ Synopsis

Several syntheses of thromboxane B2' (1,, vla prostarwld precursors' or dIrectly3 have been devised.

We now describe a new and very practical direct route to j starting from the lnexpenslve, optically active precursor c-methyl-&&moslde 2). This note has been written and submitted fbr publlcatfon following recent reports 4,5 of a different synthesis of thrombcxane B2 from the sugar derlvatlve 0-benzyHdene-2deoxy-c-~~hexopyramslde.

Our synthesis commences using the known6 and efficient sequence for the conversion of2 tc the 4,5unsaturated sugar2 ([cJ23B + 61.3" in CHQ3) vla intermediates 2 and 5 The allyllc alcohols was trans-

πŸ“œ SIMILAR VOLUMES

Synthesis of Thromboxane A2 Models from
Synthesis of Thromboxane A2 Models from Glucose. II. Epoxidation Studies of Hex-2-enopyranosides
✍ Cirelli, Alicia FernΓ‘ndez ;Moradei, Oscar ;Thiem, Joachim πŸ“‚ Article πŸ“… 1997 πŸ› John Wiley and Sons 🌐 English βš– 458 KB

## Abstract The synthesis of halohydrin 7, a potential precursor of the heterocyclic moiety of thromboxane A~2~ (TXA~2~) is described. Claisen‐Meerwein‐Eschenmoser rearrangement of hex‐3‐enopyranosides 4 and 8 yields the branched olefin sugars 5 and 9. Epoxidation studies with perbenzimidic acid (P