A model study for the total synthesis of (+/-)-scopadulin: stereoselective construction of the A/B ring system with desired functionalities
A model study toward the total synthesis of (+/-)-scopadulin is described. Stereocontrolled synthesis of the A/B ring system with desired functionalities was achieved by stereoselective cyanation of a bicyclic enone with Et2AlCN, diastereoselective construction of a quaternary carbon at C-4 with LDA...
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| Published in | Tetrahedron Vol. 57; no. 1; pp. 127 - 134 |
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| Main Authors | , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
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Elsevier
01.01.2001
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| Abstract | A model study toward the total synthesis of (+/-)-scopadulin is described. Stereocontrolled synthesis of the A/B ring system with desired functionalities was achieved by stereoselective cyanation of a bicyclic enone with Et2AlCN, diastereoselective construction of a quaternary carbon at C-4 with LDA-BOMCl, and conversion of the cyano group into a methyl group. (C) 2000 Elsevier Science Ltd. All rights reserved. |
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| AbstractList | A model study toward the total synthesis of (+/-)-scopadulin is described. Stereocontrolled synthesis of the A/B ring system with desired functionalities was achieved by stereoselective cyanation of a bicyclic enone with Et2AlCN, diastereoselective construction of a quaternary carbon at C-4 with LDA-BOMCl, and conversion of the cyano group into a methyl group. (C) 2000 Elsevier Science Ltd. All rights reserved. |
| Author | Tanaka, T Tsukaguchi, M Yoshino, H Satoh, N Murakami, K Maezaki, N Rahman, SMA Ohno, H Iwata, C |
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| Keywords | STEMODANE DITERPENES (+/-)-APHIDICOLIN SCOPARIA-DULCIS L APHIDICOLANE diastereoselection conjugate addition deamination copper and compounds FORMAL TOTAL SYNTHESIS ACID-B |
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| Title | A model study for the total synthesis of (+/-)-scopadulin: stereoselective construction of the A/B ring system with desired functionalities |
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