Gajula, Srinivas ; Vishnu V. Reddy, Aedula ; Reddy, D. Prabhakar ; Yadav, Jhillu S. ; Mohapatra, Debendra K. (2020) Stereoselective Synthesis of the C1–C16 Fragment of the Purported Structure of Formosalide B ACS Omega, 5 (17). pp. 10217-10224. ISSN 2470-1343
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Official URL: http://doi.org/10.1021/acsomega.0c01474
Related URL: http://dx.doi.org/10.1021/acsomega.0c01474
Abstract
The first stereoselective synthesis of the C1-C16 fragment possessing stereo-enriched fully substituted tetrahydropyran (THP) along with tetrahydrofuran (THF) rings of the proposed structure of formosalide B is described in 12 longest linear steps with 22% overall yield, starting from two cheap and commercially available 1,5-pentanediol and l-glutamic acid, following a convergent approach. The key steps involve in this synthesis are Horner-Wadsworth-Emmons reaction, Sharpless asymmetric dihydroxylation, and acid-mediated ketalization to assemble the substituted THP ring, one-pot Sharpless dihydroxylation-SN2-type cyclization, and Wittig homologation to construct the THF derivative.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 135659 |
| Deposited On: | 17 Jul 2023 07:56 |
| Last Modified: | 17 Jul 2023 07:56 |
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