Concepedia

Total synthesis and stereochemical revision of lagunamide A

Lu Dai, Bo Chen, Honghui Lei, Zhuo Wang, Yuqing Liu, Zhengshuang Xu, Tao Ye

Chemical Communications · 2012 · 58 citations · 29 references

Concepts

Natural SciencesChemistryMarine SciencesBioisosterismMetabolite IdentificationRetrosynthetic AnalysisBioactive Marine MetabolitesConfigurational AssignmentMarine Compound Structure ElucidationMarine Microbial Secondary MetabolitesMarine Sponge MetabolitesNatural Product Total SynthesisStereochemical ValidationTotal Synthesis-derived Analogues

Abstract

A revised configurational assignment for the marine metabolite lagunamide A is proposed and validated by total synthesis.

References

29

1-Hydroxy-7-azabenzotriazole. An efficient peptide coupling additive

Louis A. Carpino · Journal of the American Chemical Society · 1993 · 1.5K citations

Natural Sciences, Chemistry, Pharmacology +7

Stereochemistry of alternating polyol chains: 13C NMR analysis of 1,3-diol acetonides

Scott D. Rychnovsky, Donald J. Skalitzky · Tetrahedron Letters · 1990 · 478 citations

Natural Sciences, Biochemistry, Chemistry +7

Enantiomeric Z- and E-crotyldiisopinocampheylboranes. Synthesis in high optical purity of all four possible stereoisomers of .beta.-methylhomoallyl alcohols

Herbert C. Brown, K. S. BHAT · Journal of the American Chemical Society · 1986 · 324 citations

Natural Sciences, Chemistry, Carbohydrate Chemistry +5

A FACILE CLEAVAGE OF BENZYLIDENE ACETALS WITH DIISOBUTYLALUMINUM HYDRIDE

Seiichi Takano, Masashi Akiyama, Seiji Sato et al. · Chemistry Letters · 1983 · 184 citations

Natural Sciences, Chemistry, Organic Chemistry +5

Stereochemical consequences for the Lewis acid mediated additions of allyl and crotyltri--butylstannane to chiral β-hydroxyaldehyde derivatives

Gary E. Keck, D. E. ABBOTT · Tetrahedron Letters · 1984 · 156 citations

Natural Sciences, Chemistry, Organic Chemistry +11