Journal article
Synthesis of (−)-6,7-dideoxysqualestatin H5 by carbonyl ylide cycloaddition–rearrangement and cross-electrophile coupling
- Abstract:
-
An asymmetric synthesis of (−)-6,7-dideoxysqualestatin H5 is reported. Key features of the synthesis include: (1) highly diastereoselective n-alkylation of a tartrate acetonide enolate and subsequent oxidation−hydrolysis to provide an asymmetric entry to a β-hydroxy-α-ketoester motif; (2) facilitation of Rh(II)-catalyzed cyclic carbonyl ylide formation−cycloaddition by cogeneration of keto and diazo functionality through ozonolysis of an unsaturated hydrazone; and (3) stereoretentive Ni-catal...
Expand abstract
- Publication status:
- Published
- Peer review status:
- Peer reviewed
Actions
Access Document
- Files:
-
-
(Preview, Version of record, pdf, 955.8KB, Terms of use)
-
- Publisher copy:
- 10.1021/acs.orglett.7b01513
Authors
Funding
Bibliographic Details
- Publisher:
- American Chemical Society
- Journal:
- Organic Letters More from this journal
- Volume:
- 19
- Issue:
- 13
- Pages:
- 3540–3543
- Publication date:
- 2017-06-20
- Acceptance date:
- 2017-06-14
- DOI:
- EISSN:
-
1523-7052
- ISSN:
-
1523-7060
Item Description
- Pubs id:
-
pubs:700636
- UUID:
-
uuid:8023d4d7-1826-437a-a6ab-99c25524cd3c
- Local pid:
-
pubs:700636
- Source identifiers:
-
700636
- Deposit date:
-
2017-06-15
Terms of use
- Copyright holder:
- American Chemical Society
- Copyright date:
- 2017
- Notes:
- © 2017 American Chemical Society. ACS AuthorChoice - This is an open access article published under a Creative Commons Attribution (CC-BY) License, which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
- Licence:
- CC Attribution (CC BY)
Metrics
If you are the owner of this record, you can report an update to it here: Report update to this record