SYNTHESIS OF ENDO-1,3-DIMETHYL-2,9-DIOXABICYCLO-(3.3.1)NONANE

摘要

PURPOSE:To obtain the titled compound useful as an attractant of wood borer, in high yield and stereo-selectivity, by using (-)-(R)-1,3-butanediol as a starting substance of successive reaction steps. CONSTITUTION:The objective compound of formula II can be prepared by (1) treating the compound of formula I with lithium isopropylamine and CH3COO (t-C4H9), (2) oxidizing the product, (3) treating with a dithiol in the presence of a Lewis acid, (4) treating with lithium diisopropylamine and CH3COO(t-C4H9), (5) reacting with camphor sulfonic acid and CH(OCH3)3, (6) dedithiolating and reducing the reaction product, (7) reacting with a dithiol in the presence of a Lewis acid and then with CH3OCH2Cl, (8) treating with Raney nickel and then with methyl lithium, and finally (9) refluxing under acidic condition and treating with an acid.