Prasad, Kavirayani R. ; Gandi, Vasudeva Rao ; Nidhiry, John Eugene ; Bhat, Kavya S. (2010) Enantiodivergent formal total synthesis of aspercyclide C from l-(+)-tartaric acid Synthesis, 2010 (15). pp. 2521-2526. ISSN 0039-7881
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Official URL: https://www.thieme-connect.com/products/ejournals/...
Related URL: http://dx.doi.org/10.1055/s-0029-1218831
Abstract
The enantiodivergent formal syntheses of both enantiomers of aspercyclide C is accomplished. Starting from l-(+)-tartaric acid, the key protected allylic alcohol, (3R,4R)-4-(methoxymethoxy)non-1-en-3-ol is prepared, and is then elaborated into both enantiomers of 3-[(4-methoxybenzyl)oxy]non-1-en-4-ol via Mitsunobu inversion. Esterification with a known biaryl acid, followed by ring-closing metathesis and deprotection completes the syntheses.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Thieme Medical Publishers Inc. |
| Keywords: | Aspercyclide C; Total Synthesis; Tartaric Acid; Mitsunobu Inversion; Ring-closing Metathesis |
| ID Code: | 105713 |
| Deposited On: | 21 Dec 2017 12:05 |
| Last Modified: | 21 Dec 2017 12:05 |
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