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CC BY-ND-NC 4.0 · SynOpen 2017; 01(01): 0166-0172
DOI: 10.1055/s-0036-1591844
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Synthesis of the C1–C9, C11–C19 Pyran Core and C19–C24 Fragments­ of Macrolactin 3

A. Maheshwar Reddy
a   Natural Products Chemistry Division and CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India
b   Academy of Scientific and Innovative Research (AcSIR), New Delhi 110020, India   Email: gowravaramsr@yahoo.com
,
Gowravaram Sabitha*
a   Natural Products Chemistry Division and CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India
b   Academy of Scientific and Innovative Research (AcSIR), New Delhi 110020, India   Email: gowravaramsr@yahoo.com
› Author AffiliationsA.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).
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Publication History

Received: 17 October 2017

Accepted after revision: 07 November 2017

Publication Date:
29 November 2017 (online)

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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-ribose

Supporting 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.
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