Stereoselective Total Synthesis of Pectinolides A, C, and H

Ghogare, Ramesh S.; Wadavrao, Sachin B.; Narsaiah, A. Venkat

doi:10.1002/hlca.201500110

Cited by 8 publications

(4 citation statements)

References 15 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…With the azide 14 in hand, selective cleavage of the primary TBS-ether was then explored. A variety of traditional methods including CSA/MeOH, 13 TsOH/MeOH, 14 and conc. HCl/CHCl 3 (ref.…”

Section: -Methylprolinesmentioning

confidence: 99%

Highly stereoselective gram scale synthesis of all the four diastereoisomers of Boc-protected 4-methylproline carboxylates

et al. 2019

View full text Add to dashboard Cite

show abstract

“…With the azide 14 in hand, selective cleavage of the primary TBS-ether was then explored. A variety of traditional methods including CSA/MeOH, 13 TsOH/MeOH, 14 and conc. HCl/CHCl 3 (ref.…”

Section: -Methylprolinesmentioning

confidence: 99%

Highly stereoselective gram scale synthesis of all the four diastereoisomers of Boc-protected 4-methylproline carboxylates

et al. 2019

View full text Add to dashboard Cite

show abstract

“…Complementary structural information was available via the utility of the DFT chemical shifts and 3 J H,H calculations in the gas phase and CHCl 3 solution for the conformational analysis and epimer differentiation of compounds 3 and 5 by taking advantage of the fact that the absolute configuration for pectinolide C ( 3 ) has also been confirmed by stereoselective total synthesis . The 1 H NMR chemical shifts and coupling constants were sufficiently different between this natural product and its epimeric counterpart at C-3′, pectinolide J ( 5 ), to permit the appropriate spectroscopic interpretation of each stereoisomer after comparison with the DFT 1 H NMR chemical shifts and 3 J H,H values.…”

Section: Resultsmentioning

confidence: 99%

Structure Elucidation, Conformation, and Configuration of Cytotoxic 6-Heptyl-5,6-dihydro-2H-pyran-2-ones from Hyptis Species and Their Molecular Docking to α-Tubulin

et al. 2019

View full text Add to dashboard Cite

Cytotoxic 6-heptyl-5,6-dihydro-2H-pyran-2-ones are chemical markers of Hyptis (Lamiaceae) and are responsible for some of the therapeutic properties of species with relevance to traditional medicine. The present investigation describes the isolation of known pectinolides A–C (1–3), in addition to the new pectinolides I–M (4–8), from two Mexican collections of H. pectinata by HPLC. The novel biosynthetically related monticolides A (9) and B (10) were also isolated by high-speed countercurrent chromatography from H. monticola, an endemic species of the Brazilian southeastern high-altitude regions. A combination of chemical correlations, chiroptical measurements, and Mosher ester NMR analysis was used to confirm their absolute configuration. The utility of DFT-NMR chemical shifts and J H–H calculations was assessed for epimer differentiation. Molecular docking studies indicated that 6-heptyl-5,6-dihydro-2H-pyran-2-ones have a high affinity for the pironetin-binding site of α-tubulin, which may be a possible mechanism contributing to the cytotoxic potential of these small and flexible molecules.

show abstract

“…As part of our regular research program for the synthesis of biologically active natural products, [5][6][7][8] herein we report the formal stereoselective synthesis of aspergillide D. The retrosynthetic analysi s (Scheme 1) reveals that aspergillide D could be synthesized by intramolecular macrolactonisation of fragment 16. The ester (16) could be derived by the coupling of alkyne (3) and iodide fragments (12).…”

Section: Resultsmentioning

confidence: 99%