The title compound was synthesized using a novel approach to form a C3.2.11 oxabicyclic ring system. This was achieved through an intramolecular C-H insertion of a carbenoid intermediate. ## Endo -1,3-dimethyl-2,9-dioxabicycloC3.3.11 nonane 1. isolated from Norway spruce, was found to be a host s
Synthetic utility of chiral tetrahydrofurans: Preparation of (1R, 3R, 5S)-1, 3-dimethyl-2, 9-dioxabicyclo[3.3.1]nonane
✍ Scribed by Yvan Guindon; Yves St. Denis; Sylvain Daigneault; Howard E. Morton
- Publisher
- Elsevier Science
- Year
- 1986
- Tongue
- French
- Weight
- 246 KB
- Volume
- 27
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The use of the lodoetherlflcatlon reaction for the selective preparatlon of optically active w-2,4-dlsubstltuted tetrahydrofurans and the use of the latter compounds as precursors of s-1,3-dlols 1s exempllfled In the synthesis of (lR,3R,5S)-~-1,3-Dlmethyl-2,9-Dloxabicyclo [3.3.l]nonane(]).
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La protection des fonctions hydroxy par 0-silylation ne permet pas d'obtenir la transformation ultirieure en (3R,5R)-5.
An efficient synthesis of a 2,9-dioxabicyclo[3.3.l]nonane system, similar to that of tirandamycin, is accomplished from 2,3\_dimethylfuran. Tirandamycin ls2 (1) is a member of the 3-acyl tetramic acid family of antibiotics which -1,3 includes streptolydigin 4 , nocamycin , antibiotics Bu-2313 A and