Font Size: a A A

Enantioselective total synthesis of borrelidin: Application of the asymmetric reductive aldol reaction

Posted on:2004-08-25Degree:Ph.DType:Thesis
University:The University of North Carolina at Chapel HillCandidate:Duffey, Matthew OwenFull Text:PDF
GTID:2461390011966625Subject:Chemistry
Abstract/Summary:
The first asymmetric reductive aldol reaction is reported. The synthetic utility of this transformation is demonstrated through its use in the enantioselective total synthesis of borrelidin, a macrolide antibiotic. The total synthesis of borrelidin was achieved through a convergent strategy with the longest linear sequence being 35 steps and an overall yield of 0.6%.
Keywords/Search Tags:Total synthesis, Borrelidin
Related items
1 The application of asymmetric catalysis to the synthesis of natural products: A total synthesis of (-)-tubulosine, progress towards a total synthesis of (+)-reserpine, and a total synthesis of (+)-peloruside A
2 New methods and strategies for heterocycle synthesis: Progress toward the total synthesis of upenamide and the total synthesis of (+)-5-epiindolizidine 167B and indolizidine 223AB
3 Total synthesis of ht-13-A and ht-13-B, total synthesis of aurantioclavine, progress towards the synthesis of cycloclavine
4 Enantiospecific stereospecific total synthesis of the oxindole alkaloid (+)-alstonisine and stereocontrolled total synthesis of (-)-11-methoxy-17-epivincamajine as well as studies directed toward the total synthesis of N(b)-demethylalstophylline oxindole
5 Part I: The first regio- and atropdiastereoselective total synthesis of the dimeric indole alkaloid (+)-dispegatrine, as well as the first total synthesis of the sarpagine alkaloids (+)-spegatrine, lochvinerine, (+)-lochneram and an improved total synthes
6 Total Syntheses Of (+)-Agelastatin A And B, Longifolene And (+)-Minfiensine, And Studies Toward Total Synthesis Of Daphniyunnine C
7 One-Pot Total Synthesis Of Natural Products And New Synthetic Methodology Of Relative N-Containing Heterocycles From Amino Acids
8 I. Total synthesis of trichoaurantianolide C and D II. Studies toward the total synthesis of norzoanthamine
9 Asymmetric Total Synthesis of Cylindrocyclophanes A and F through Cyclodimerization and a Ramberg--Backlund Reaction and Studies Directed Towards the Total Synthesis of CJ-16,264
10 The total synthesis of biologically active C-glycoside natural products: 1) Total synthesis of (-)-centrolobine 2) Total synthesis of (-)-varitriol and analogues 3) Progress towards the total synthesis of polyrhacatide A