Alkene protection against acid using a bromide substituent: application in a total synthesis of (−)-6,7-dideoxysqualestatin H5-Reference-Cited by-同舟云学术

Alkene protection against acid using a bromide substituent: application in a total synthesis of (−)-6,7-dideoxysqualestatin H5

Published:2018 Issue:42 Volume:54 Page:5354-5356
ISSN:1359-7345
Container-title:Chemical Communications
language:en
Short-container-title:Chem. Commun.

Author:

Almohseni Hasanain A. A.¹²³⁴⁵,Al Mamari Hamad H.¹²³⁴⁵,Valade Anne¹²³⁴⁵,Sintim Herman O.¹²³⁴⁵^ORCID,Hodgson David M.¹²³⁴⁵^ORCID

Affiliation:

1. Department of Chemistry

2. Chemistry Research Laboratory

3. University of Oxford

4. Oxford OX1 3TA

5. UK

Abstract

Alkenyl bromide functionality survives several synthetic steps, including an acid-induced rearrangement, before a stereoretentive methylative debromination gives the natural product.

Funder

Sixth Framework Programme

Higher Committee for Education Development in Iraq

University of Oxford

Publisher

Royal Society of Chemistry (RSC)

Subject

Materials Chemistry,Metals and Alloys,Surfaces, Coatings and Films,General Chemistry,Ceramics and Composites,Electronic, Optical and Magnetic Materials,Catalysis

Link

http://pubs.rsc.org/en/content/articlepdf/2018/CC/C8CC02690D

Reference25 articles.

1. Recent synthetic studies on the zaragozic acids (squalestatins)

2. Novel Approach to the Zaragozic Acids. Enantioselective Total Synthesis of 6,7-Dideoxysqualestatin H5

3. Synthesis of (−)-6,7-Dideoxysqualestatin H5 by Carbonyl Ylide Cycloaddition–Rearrangement and Cross-electrophile Coupling

4. Suzuki reactions of extended scope: the ‘9-MeO-9-BBN variant’ as a complementary format for cross-coupling

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