Handore, Kishor L. ; Seetharamsingh, B. ; Reddy, D. Srinivasa (2013) Ready Access to Functionally Embellished cis-Hydrindanes and cis-Decalins: Protecting Group-Free Total Syntheses of (±)-Nootkatone and (±)-Noreremophilane Journal of Organic Chemistry, 78 (16). pp. 8149-8154. ISSN 0022-3263
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Official URL: http://doi.org/10.1021/jo401033j
Related URL: http://dx.doi.org/10.1021/jo401033j
Abstract
A simple and efficient synthesis of functionalized cis-hydrindanes and cis-decalins was achieved using a sequential Diels–Alder/aldol approach in a highly diastereoselective manner. The scope of this method was tested with a variety of substrates and was successfully applied to the synthesis of two natural products in racemic form. The highlights of the present work provide ready access to 13 new cis-hydrindanes/cis-decalins, a protecting group-free total synthesis of an insect repellent Nootkatone, and the first synthesis of a Noreremophilane using the shortest sequence.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society |
| ID Code: | 121960 |
| Deposited On: | 23 Jul 2021 10:23 |
| Last Modified: | 23 Jul 2021 10:23 |
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