Mohapatra, Debendra K. ; Pulluri, Karthik ; Gajula, Srinivas ; Yadav, Jhillu S. (2015) 13-Step total synthesis of Dendrodolide K following iterative Bartlett–Smith iodocarbonate cyclization Tetrahedron Letters, 56 (46). pp. 6377-6380. ISSN 0040-4039
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Official URL: http://doi.org/10.1016/J.Tetlet.2015.09.126
Related URL: http://dx.doi.org/10.1016/J.Tetlet.2015.09.126
Abstract
A convergent total synthesis of Dendrodolide K has been achieved starting from commercially available homoallyl alcohol 17 in 13 longest linear sequence with 18.2% overall yield. The key features of this synthesis are Bartlett–Smith iodocarbonate cyclization reaction for the construction of 1,3-syn centers of the polyol system, Sharpless epoxidation followed by titanocene induced deoxygenation of 2,3-epoxy alcohol to fix stereogenic center at C-3 position, Yamaguchi esterification followed by ring-closing metathesis (RCM) reaction to form the macrolactone.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| ID Code: | 135711 |
| Deposited On: | 10 Aug 2023 10:29 |
| Last Modified: | 10 Aug 2023 10:29 |
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