Language:

Multifunctional organoboron compounds for scalable natural product synthesis

Nature (London), 2014-09, Vol.513 (7518), p.367-374 [Peer Reviewed Journal]

COPYRIGHT 2014 Nature Publishing Group ;COPYRIGHT 2014 Nature Publishing Group ;Copyright Nature Publishing Group Sep 18, 2014 ;ISSN: 0028-0836 ;EISSN: 1476-4687 ;DOI: 10.1038/nature13735 ;PMID: 25230659 ;CODEN: NATUAS

Full text available

Citations Cited by

Actions
1. Add to My Research
2. Remove from My Research
3. E-mail
4. Print
5. Permalink
6. Citation
7. EasyBib
8. EndNote
9. RefWorks
10. Delicious
11. Export RIS
12. Export BibTeX

Title:
Multifunctional organoboron compounds for scalable natural product synthesis
Author: Meng, Fanke ; McGrath, Kevin P ; Hoveyda, Amir H
Subjects: Alkenes - chemical synthesis ; Alkenes - chemistry ; Animals ; Anti-Bacterial Agents - chemical synthesis ; Anti-Bacterial Agents - chemistry ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Biological Products - chemical synthesis ; Biological Products - chemistry ; Boron ; Boron - chemistry ; Catalysis ; Chemical properties ; Chemical synthesis ; Copper - chemistry ; Fatty Alcohols - chemical synthesis ; Fatty Alcohols - chemistry ; Methods ; Monosaccharides - chemical synthesis ; Monosaccharides - chemistry ; Natural products ; Organoboron compounds ; Phosphates ; Porifera - chemistry ; Production processes ; Pyrans - chemical synthesis ; Pyrans - chemistry ; Stereoisomerism
Is Part Of: Nature (London), 2014-09, Vol.513 (7518), p.367-374
Description: Efficient catalytic reactions that can generate C-C bonds enantioselectively, and ones that can produce trisubstituted alkenes diastereoselectively, are central to research in organic chemistry. Transformations that accomplish these two tasks simultaneously are in high demand, particularly if the catalysts, substrates and reagents are inexpensive and if the reaction conditions are mild. Here we report a facile multicomponent catalytic process that begins with a chemoselective, site-selective and diastereoselective copper-boron addition to a monosubstituted allene; the resulting boron-substituted organocopper intermediates then participate in a similarly selective allylic substitution. The products, which contain a stereogenic carbon centre, a monosubstituted alkene and an easily functionalizable Z-trisubstituted alkenylboron group, are obtained in up to 89 per cent yield, with more than 98 per cent branch-selectivity and stereoselectivity and an enantiomeric ratio greater than 99:1. The copper-based catalyst is derived from a robust heterocyclic salt that can be prepared in multigram quantities from inexpensive starting materials and without costly purification procedures. The utility of the approach is demonstrated through enantioselective synthesis of gram quantities of two natural products, namely rottnestol and herboxidiene (also known as GEX1A).
Publisher: England: Nature Publishing Group
Language: English
Identifier: ISSN: 0028-0836
EISSN: 1476-4687
DOI: 10.1038/nature13735
PMID: 25230659
CODEN: NATUAS
Source: ProQuest One Psychology
MEDLINE
ProQuest Central

Back to results list


INSPIRE LIBRARY - TON DUC THANG UNIVERSITY	(84-028) 37 755 057	Feedback
19 Nguyen Huu Tho St. Dist.7, HCM	thuvien@tdtu.edu.vn	Feedback

Multifunctional organoboron compounds for scalable natural product synthesis

COPYRIGHT 2014 Nature Publishing Group ;COPYRIGHT 2014 Nature Publishing Group ;Copyright Nature Publishing Group Sep 18, 2014 ;ISSN: 0028-0836 ;EISSN: 1476-4687 ;DOI: 10.1038/nature13735 ;PMID: 25230659 ;CODEN: NATUAS

Searching Remote Databases, Please Wait