Studies on the Synthesis of Tedanolide. 2. Stereoselective Synthesis of a Protected C(1)−C(12) Fragment

Highly diastereoselective syntheses of diketo esters 6a and 6b are described. These intermediates undergo efficient aldol reactions with protected C(13)−C(21) aldehydes 3 and 23, thereby providing advanced C(1)−C(21) tedanolide seco ester precursors 9a and 9b.

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 4; no. 26; pp. 4739 - 4742
Main Authors Roush, William R, Newcom, Jason S
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 26.12.2002
Amer Chemical Soc
Subjects
Aldehydes - chemistry
Animals
Antineoplastic Agents - chemical synthesis
Chemistry
Chemistry, Organic
Esters - chemistry
Lactones - chemical synthesis
Macrolides - chemical synthesis
Physical Sciences
Porifera - chemistry
Science & Technology
Stereoisomerism
ALDOL ALDOL PROCESS
18-MEMBERED ANTITUMOR MACROLIDE
REDUCTION
EFFICIENT SHARPLESS DIHYDROXYLATION
SECO-ACID
ESTERS
CONSTRUCTION
C-13-C23 PART
MACROLACTONIZATION
C1-C7 FRAGMENT
Online AccessGet full text

Cover

More Information
Summary:Highly diastereoselective syntheses of diketo esters 6a and 6b are described. These intermediates undergo efficient aldol reactions with protected C(13)−C(21) aldehydes 3 and 23, thereby providing advanced C(1)−C(21) tedanolide seco ester precursors 9a and 9b.
Bibliography:Medline
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0272343