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Concise synthesis of calystegines B2 and B3via intramolecular Nozaki–Hiyama–Kishi reaction

Abstract:
The key step in the concise syntheses of calystegine B2 and its C-2 epimer calystegine B3 was the construction of cycloheptanone 8via an intramolecular Nozaki-Hiyama-Kishi (NHK) reaction of 9, an aldehyde containing a Z-vinyl iodide. Vinyl iodide 9 was obtained by the Stork olefination of aldehyde 10, derived from carbohydrate starting materials. Calystegines B2 (3) and B3 (4) were synthesized from d-xylose and l-arabinose derivatives respectively in 11 steps in excellent overall yields (27% and 19%).
Publication status:
Published
Peer review status:
Peer reviewed
Version:
Accepted manuscript

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Publisher copy:
10.1039/c6ob00697c

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
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Funding agency for:
Fleet, GWJ
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Grant:
“Major New Drugs Innovation and Development” (2013ZX09508104)
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Publisher:
Royal Society of Chemistry Publisher's website
Journal:
Organic and Biomolecular Chemistry Journal website
Volume:
14
Issue:
21
Pages:
4885-4896
Publication date:
2016-05-03
DOI:
EISSN:
1477-0539
ISSN:
1477-0520
URN:
uuid:cd4459f5-5a6f-469c-86f6-adf801c8114f
Source identifiers:
628061
Local pid:
pubs:628061

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