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手性金（I）-冠醚对 1,6-烯炔的对映选择性烷氧基环化反应：马法切宁 C 的全合成。

Enantioselective Alkoxycyclization of 1,6-Enynes with Gold(I)-Cavitands: Total Synthesis of Mafaicheenamine C.

机构信息

Institute of Chemical Research of Catalonia (ICIQ), Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007, Tarragona, Spain.

Departament de Química Analítica i Química Orgànica, Universitat Rovira i Virgili, C/ Marcel⋅lí Domingo s/n, 43007, Tarragona, Spain.

出版信息

Angew Chem Int Ed Engl. 2021 Apr 19;60(17):9339-9344. doi: 10.1002/anie.202017035. Epub 2021 Mar 11.

DOI:10.1002/anie.202017035
PMID:33576560
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8251978/
Abstract

Chiral gold(I)-cavitand complexes have been developed for the enantioselective alkoxycyclization of 1,6-enynes. This enantioselective cyclization has been applied for the first total synthesis of carbazole alkaloid (+)-mafaicheenamine C and its enantiomer, establishing its configuration as R. The cavity effect was also evaluated in the cycloisomerization of dienynes. A combination of experiments and theoretical studies demonstrates that the cavity of the gold(I) complexes forces the enynes to adopt constrained conformations, which results in the high observed regio- and stereoselectivities.

摘要

手性金（I）-环糊精配合物已被开发用于 1,6-烯炔的对映选择性烷氧基环化反应。这种对映选择性环化反应首次应用于咔唑生物碱 (+)-mafaicheenamine C 及其对映异构体的全合成，确定了其构型为 R。空腔效应也在二烯炔的环异构化中进行了评估。实验和理论研究的结合表明，金（I）配合物的空腔迫使烯炔采取受限构象，从而导致高观察到的区域和立体选择性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c449/8251978/592d28b687c5/ANIE-60-9339-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c449/8251978/b3985ec74bad/ANIE-60-9339-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c449/8251978/21b6f4f27c84/ANIE-60-9339-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c449/8251978/acae84317f68/ANIE-60-9339-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c449/8251978/29c12df41b00/ANIE-60-9339-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c449/8251978/61ef754cec50/ANIE-60-9339-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c449/8251978/592d28b687c5/ANIE-60-9339-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c449/8251978/b3985ec74bad/ANIE-60-9339-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c449/8251978/21b6f4f27c84/ANIE-60-9339-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c449/8251978/acae84317f68/ANIE-60-9339-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c449/8251978/29c12df41b00/ANIE-60-9339-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c449/8251978/61ef754cec50/ANIE-60-9339-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c449/8251978/592d28b687c5/ANIE-60-9339-g008.jpg

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