Journal article
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
Actions
Access Document
- Files:
-
-
(Accepted manuscript, pdf, 426.8KB)
-
- Publisher copy:
- 10.1039/c6ob00697c
Why is the content I wish to access not available via ORA?
Bibliographic data (the information relating to research outputs) and full-text items (e.g. articles, theses, reports, etc.) arrive in ORA from several different sources. Unfortunately we are not able to make available the full-text for every research output.
Please contact the ORA team (
) if you have queries regarding unavailable content OR if you are aware of a full-text copy we can make available.
) if you have queries regarding unavailable content OR if you are aware of a full-text copy we can make available.
Content may be unavailable for the following four reasons
-
Version unsuitable
-
We have not obtained a suitable full-text for a given research output. See this page for more information.
-
Recently completed
-
Sometimes content is held in ORA but is unavailable for a fixed period of time to comply with the policies and wishes of rights holders.
-
Permissions
-
All content made available in ORA should comply with relevant rights, such as copyright. See this page for more information.
-
Clearance
-
Some thesis volumes scanned as part of the digitisation scheme funded by Dr Leonard Polonsky are currently unavailable due to sensitive material or uncleared third-party copyright content. We are attempting to contact authors whose theses are affected.
Alternative access to the full-text
You may be able to access the full-text directly from the publisher's website using the 'Publisher Copy' link in the 'Links & Downloads' box from a research output's ORA record page. This method may require an institutional or individual subscription to the journal/resource.
Authors
Funding
+ National Science and Technology Major Projects
More from this funder
Grant:
“Major New Drugs Innovation and Development” (2013ZX09508104)
Chinese Academy of Science
More from this funder
Expand funders...
Bibliographic Details
- 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
- Acceptance date:
- 2016-04-28
- DOI:
- EISSN:
-
1477-0539
- ISSN:
-
1477-0520
- Source identifiers:
-
628061
Item Description
- Pubs id:
-
pubs:628061
- UUID:
-
uuid:cd4459f5-5a6f-469c-86f6-adf801c8114f
- Local pid:
- pubs:628061
- Deposit date:
- 2016-07-04
Terms of use
- Copyright holder:
- Wang et al
- Copyright date:
- 2016
- Notes:
- © the Author(s). This journal is © The Royal Society of Chemistry 2017.
If you are the owner of this record, you can report an update to it here: Report update to this record