Department of Organic Chemistry Faculty of Pharmacy, University of Granada, 18071, Granada, Spain.
J Chem Ecol. 1992 Feb;18(2):115-25. doi: 10.1007/BF00993747.
The synthesis of (3S,6R)-3-hydroxy-1,7-dioxaspiro[5.5]undecane (8) and its (4R)-4-hydroxy isomer (11) from (3R,4S,6R)-3,4-dihydroxy-1,7-dioxaspiro[5.5]undecane (1), obtained from D-fructose, has been accomplished by regioselective deoxygenation at C-4 and C-3, respectively, of the appropriately protected derivatives.
(3S,6R)-3-羟基-1,7-二氧杂螺[5.5]十一烷(8)及其(4R)-4-羟基异构体(11)可分别由(3R,4S,6R)-3,4-二羟基-1,7-二氧杂螺[5.5]十一烷(1)(来源于 D-果糖)经区域选择性脱氧得到,其中相应保护的衍生物的 C-4 和 C-3 位分别进行了脱氧反应。