Synthesis of 15-Hydroxypentadecanoic and 16-hydroxyhexadecanoic acids

Nesmeyanov, A. N.; Zakharkin, L. I.; Kost, Thomas A.; Friedlina, R. Kh.

doi:10.1007/bf00942889

Search citation statements

Order By: Relevance

Paper Sections

Select...

Results1

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2012

Publication Types

Select...

Article1

Relationship

Self Cite0

Independent1

Authors

Journals

Cited by 1 publication

(1 citation statement)

References 2 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Notably, a previously synthesised LI-F04a analogue with a twelve-carbon side chain lacking the hydroxy group has been observed to have antimicrobial activity [ 9 ]. Thus, hydrolysis of pentadecanolide 13 [ 26 ] was followed by esterification to give the methyl ester 14 in excellent yield. Reaction of 14 with di( tert -butoxycarbonyl)guanidine under Mitsunobu conditions [ 27 ] proceeded smoothly to give 15 in 86% yield.…”

Section: Resultsmentioning

confidence: 99%

A macrolactonization approach to the total synthesis of the antimicrobial cyclic depsipeptide LI-F04a and diastereoisomeric analogues

Cochrane¹,

Yoon²,

McErlean³

et al. 2012

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

SummaryThe cyclic peptide core of the antifungal and antibiotic cyclic depsipeptide LI-F04a was synthesised by using a modified Yamaguchi macrolactonization approach. Alternative methods of macrolactonization (e.g., Corey–Nicolaou) resulted in significant epimerization of the C-terminal amino acid during the cyclization reaction. The D-stereochemistry of the alanine residue in the naturally occurring cyclic peptide may be required for the antifungal activity of this natural product.

show abstract

Section: Resultsmentioning

confidence: 99%