| Autor: |
Ford, Hannah G., Hastry, Emma C., Choi, Joshua B., Terranova, Christopher J., Quinn, Kevin J. |
| Předmět: |
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| Zdroj: |
Synlett; Feb2023, Vol. 34 Issue 3, p259-262, 4p |
| Abstrakt: |
Synthesis of the originally assigned structure of the styryl tetrahydropyranol-dihydropyranone natural product cryptoconcatone H from C 2-symmetric (±)-1,8-nonadiene-4,6-diol is reported. Desymmetrization by Mitsunobu reaction with crotonic acid established the requisite inter-ring stereochemical relationship and was followed by a highly diastereoselective Re2 O7-catalyzed Prins cyclization with cinnamaldehyde to construct the 2,4,6- cis -tetrahydropyranol ring. Ring-closing metathesis resulted in formation of the dihydropyranone ring and completed the synthesis in three steps and 32% overall yield. The brevity of the synthesis is the result of the recognition of hidden, inter-ring symmetry in the target and the ensuing choice of an appropriately symmetric diol as our starting material. [ABSTRACT FROM AUTHOR] |
| Databáze: |
Complementary Index |
| Externí odkaz: |
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