Stereodivergent and reiterative synthesis of bistetrahydrofuran ring cores of annonaceous acetogenins
Stereodivergent and reiterative synthesis of bistetrahydrofuran ring cores of annonaceous acetogenins
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DOI：
10.1002/chem.200305459
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发表时间：
2004-02-06
影响因子：
4.3
通讯作者：
Tanaka, T
中科院分区：
文献类型：
--
作者：
Kojima, N;Maezaki, N;Tanaka, T
通过α-四氢呋喃醛的不对称炔基化反应和立体分散一锅法四氢呋喃（THF）成环反应，合成了番荔枝内酯类化合物双四氢呋喃环核的8个非对映异构体。在所有情况下，不对称炔基化进行了非常高的非对映选择性，得到八种光学纯的THF核。我们还描述了8个异构体的H-1和C-13 NMR光谱数据的比较，并给出了THF环结构的全部细节。
Eight diastereoisomers of the bistetrahydrofuran ring cores of annonaceous acetogenins have been synthesized by asymmetric alkynylation of alpha-tetrahydrofuranic aldehydes and stereodivergent one-pot tetrahydrofuran (THF) ring formation. In all cases, the asymmetric alkynylation proceeded with very high diastereoselectivity to give eight kinds of optically pure THF cores. We also describe a comparison of the H-1 and C-13 NMR spectral data of the eight isomers and give full details of the THF ring construction.