An organotrifluoroborate-based convergent total synthesis of the potent cancer cell growth inhibitory depsipeptides kitastatin and respirantin.

Abstract

The total syntheses of the highly cytotoxic neo-antimycin macrocyclic depsipeptide natural products kitastatin and respirantin have been accomplished in a convergent manner using MNBA promoted esterifications and an efficient C- and N-terminus bis-deprotection/HATU promoted macrolactamization. The first examples of using a prenyltrifluoroborate reagent in additions to carbonyl groups are disclosed including a diastereoselective multigram scale montmorillonite K10 catalyzed prenylation of N-Boc-l-leucinal to install the structurally unique gem-dimethyl-β-keto-ester fragment.

• Authors: Ramsay E Beveridge, Robert A Batey
• Journal: Organic letters (Org Lett) Vol. 16 Issue 9 Pg. 2322-5 (May 02 2014) ISSN: 1523-7052 [Electronic] United States
• PMID: 24730576 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Biological Products
• Borates
• Depsipeptides
• Hydrocarbons, Fluorinated
• kitastatin 1
• respirantin
• Antimycin A
• leucinal
• Leucine

Topics

• Antimycin A (analogs & derivatives, chemical synthesis)
• Biological Products (chemistry, pharmacology)
• Borates (chemistry)
• Depsipeptides (chemical synthesis, chemistry, pharmacology)
• Hydrocarbons, Fluorinated (chemistry)
• Leucine (analogs & derivatives, chemistry)
• Molecular Structure