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Stereoselective synthesis of endo-1,3 dimethyl-2,9 dioxabicyclo[3-3.1] nonane

โœ Scribed by Julian Adams; Richard Frenette

Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
135 KB
Volume
28
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

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 specific substance for the ambrosia beetle which infests the bark of the timber.' Many groups have reported the synthesis of optically active or racemic 1.2 In almost every case, the synthetic strategy relied on the formation of the dial ketone 2 or its equivalent which upon acid treatment affords the requisite bicyclic acetal.

๐Ÿ“œ SIMILAR VOLUMES

Synthesis of endo-1,3-dimethyl-2,9-dioxa
Synthesis of endo-1,3-dimethyl-2,9-dioxa-bicyclo [3.3.1.] nonane
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The title compound has been synthesized stereoselectively based on a new methodology for the construction of erythro-1,3-diols. Endo-1,3-dimethyl-2,9-dioxabicyclo[3.3.1]nonane (11, first isolated by Heemann and Francke in 1976 from Norway spruce attacked by the ambrosia beetle (Tgypodendron Lineatum

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**Synthesis of __endo__โ€ and __exo__โ€1,3โ€dimethylโ€2,9โ€dioxabicyclo[3.3.1]nonane** The synthesis of a hostโ€specific substance in norway spruce infested by __Trypodendron lineatum__ OLIV. is described (__cf. scheme 1 and 2__). Alkylation of the acetylโ€acetone diโ€anion (II) with 3โ€methylโ€3โ€butenโ€1โ€ylโ€

Synthetic utility of chiral tetrahydrofu
Synthetic utility of chiral tetrahydrofurans: Preparation of (1R, 3R, 5S)-1, 3-dimethyl-2, 9-dioxabicyclo[3.3.1]nonane
โœ Yvan Guindon; Yves St. Denis; Sylvain Daigneault; Howard E. Morton ๐Ÿ“‚ Article ๐Ÿ“… 1986 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 246 KB

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(]).