Journal article icon

Journal article

Synthesis of enantiopure dihydropyranones: aldol-based ring expansion of dihydrofurans.

Abstract:
[reaction: see text] The stereoselective Birch reduction of 3-methyl-2-furoic acids using a readily available chiral auxilairy is described; by coupling this process to an oxidative cleavage/aldol ring closure sequence we were able to produce highly functionalized and enantiopure dihydropyranones in high yield. This sequence has ample flexibility built into it, either by the use of different electrophiles during reductive alkylation or by subsequent derivatization of the dihydropyranone after ring expansion.
Publication status:
Published

Actions


Access Document


Publisher copy:
10.1021/ol0263595

Authors


More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
Expand authors...
Journal:
Organic letters
Volume:
4
Issue:
18
Pages:
3059-3062
Publication date:
2002-09-01
DOI:
EISSN:
1523-7052
ISSN:
1523-7060
Source identifiers:
32186
Language:
English
Keywords:
Pubs id:
pubs:32186
UUID:
uuid:4b4a86e7-f8f2-487f-bd14-027f32a8b68a
Local pid:
pubs:32186
Deposit date:
2012-12-19

Terms of use


Views and Downloads






If you are the owner of this record, you can report an update to it here: Report update to this record

TO TOP