Concepedia

Synthesis of the C(1)−C(25) Fragment of Amphidinol 3:  Application of the Double-Allylboration Reaction for Synthesis of 1,5-Diols

Eric M. Flamme, William Roush

Organic Letters · 2005 · 75 citations · 22 references

DOI

Concepts

Abstract

[structure: see text] A synthesis of the C(1)-C(25) fragment of amphidinol 3 is described. The synthesis features two applications of double allylboration reaction methodology for the highly stereoselective synthesis of 1,5-diol units in the C(1)-C(15) segment.

References

22

Readily accessible 12-I-5 oxidant for the conversion of primary and secondary alcohols to aldehydes and ketones

D. B. DESS, J. C. Martin · The Journal of Organic Chemistry · 1983 · 3.1K citations

, , +8

Sulfur trioxide in the oxidation of alcohols by dimethyl sulfoxide

Jekishan R. Parikh, W. von E. Doering · Journal of the American Chemical Society · 1967 · 1K citations

, , +6

The B-Alkyl Suzuki-Miyaura Cross-Coupling Reaction: Development, Mechanistic Study, and Applications in Natural Product Synthesis

Sherry R. Chemler, Dirk Trauner, Samuel J. Danishefsky · Angewandte Chemie International Edition · 2001 · 908 citations

, , +8

Synthesis of .alpha.,.beta.-unsaturated carbonyl compounds by palladium(II)-catalyzed dehydrosilylation of silyl enol ethers

Yoshihiko Ito, Toshikazu Hirao, Takeo Saegusa · The Journal of Organic Chemistry · 1978 · 861 citations

, , +5

Palladium-catalyzed inter- and intramolecular cross-coupling reactions of B-alkyl-9-borabicyclo[3.3.1]nonane derivatives with 1-halo-1-alkenes or haloarenes. Syntheses of functionalized alkenes, arenes, and cycloalkenes via a hydroboration-coupling sequence

Norio Miyaura, Tatsuo Ishiyama, Hirotomo Sasaki et al. · Journal of the American Chemical Society · 1989 · 547 citations

, , +8