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CC BY-ND-NC 4.0 · SynOpen 2017; 01(01): 0166-0172
DOI: 10.1055/s-0036-1591844
DOI: 10.1055/s-0036-1591844
paper
Synthesis of the C1–C9, C11–C19 Pyran Core and C19–C24 Fragments of Macrolactin 3
A.M.R. thanks CSIR, New Delhi, India for the award of a Fellowship. Both the authors thank CSIR, New Delhi, India for financial support as part of the XII Five Year plan programme under the title ORIGIN (CSC-0108).Weitere Informationen
Publikationsverlauf
Received: 17. Oktober 2017
Accepted after revision: 07. November 2017
Publikationsdatum:
29. November 2017 (online)
Abstract
We describe herein an efficient synthesis of the C1–C9, C11–C19 pyran moiety and C18–C24 core fragments of macrolactin 3. The prominent features of this work include construction of the Z-double bond of the 1,3-(Z,E)-diene system utilizing Horner–Wadsworth–Emmons reaction under Still–Gennari conditions. A Sharpless asymmetric epoxidation and subsequent epoxide opening under BF3·OEt2 conditions were applied to generate the stereogenic centers at C15 and C16, oxa-Michael addition and Jacobsen resolution facilitate the synthesis of the fragments.
Key words
macrolactin 3 - tetrahydropyran - BF3·OEt2 - epoxide opening - Jacobsen - oxa-Michael - d-riboseSupporting Information
- Experimental procedures, spectral data, copies of 1H NMR and 13C NMR spectra are available.Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591844.
- Supporting Information
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