从 D-果糖对映选择性合成（2S,5R）-和（2R,5R）-2-甲基-1,6-二氧杂螺[4.5]癸烷[东亚大黄蜂（L.）的气味香气次要成分]。
Enantiospecific synthesis fromD-fructose of (2S,5R)- and (2R,5R)-2-methyl-1,6-dioxaspiro[4.5]decane [the odor bouquet minor components ofParavespula vulgaris (L.)].
机构信息
Department of Organic Chemistry, Faculty of Pharmacy, University of Granada, 18071, Granada, Spain.
出版信息
J Chem Ecol. 1993 Jun;19(6):1265-83. doi: 10.1007/BF00987385.
The synthesis of (2S,5R)-(1) and (2R,5R)-2-methyl-1,6-dioxaspiro [4.5]decane (2) from (2RS,5R,8R,9R,10S)-8,9,10-trihydroxy-2-methyl-1, 6-dioxaspiro[4.5]decane (8), obtained in five steps fromD-fructose using Wittig's methodology, reduction, and spiroketalation, has been accomplished by a Corey dideoxygenation at C-8,9, followed by a Barton deoxygenation at C-10, of the appropriately protected derivatives.
（2S，5R）-（1）和（2R，5R）-2-甲基-1,6-二氧杂螺[4.5]癸烷（2）的合成本身从（2RS，5R，8R，9R，10S）-8,9,10-三羟基-2-甲基-1,6-二氧杂螺[4.5]癸烷（8）开始，通过 Wittig 法、还原和螺缩酮化，从 D-果糖中得到，共五步。通过 Corey 脱除 C-8,9 位的两个羟基，然后对相应保护的衍生物进行 Barton 脱除 C-10 位的氧，从而完成了（2S，5R）-（1）和（2R，5R）-2-甲基-1,6-二氧杂螺[4.5]癸烷（2）的合成。
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