Direct Regioselective Formation of Polysubstituted Tetrahydrofurans from Unprotected Polyols

Fujioka, Hiromichi; Kitagawa, Hirohisa; Kondo, M.; Kita, Yoshio

doi:10.3987/com-93-s116

Cited by 8 publications

(1 citation statement)

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“…Birch reduction of 2.27, synthesized from hexenal and (1S,3S)-1,3diphenyl-1,3-propanediol as shown in Chart 20, yielded optically pure 1,5-diol 2.28, which was already converted to Solenopsin A by Solladie´ and Huser. 73) (+)-(S,S)-(cis-6-Methyltetrahydropyran-2-yl) acetic acid is a constituent isolated from the perfume material civet, 74) a glandular secretion of the civet cat Viverra civetta. OsO 4 oxidation of the olefin of 2.29 followed by NaBH 4 reduction then catalytic hydrogenolysis yielded the triol 2.30.…”

Section: Intramolecular Haloetherification Of Ene Acetalsmentioning

confidence: 99%

Development of New Innovative Synthetic Organic Chemistry Using Lone Pairs of Oxygen Atoms

Fujioka

2020

CHEMICAL & PHARMACEUTICAL BULLETIN

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Oxygen atoms have a lone pair of electrons, so they have high chelation ability, high nucleophilic ability, stabilizing ability of adjacent cations, and take a chelate or oxocarbenium ion structure with Lewis acids and metals. I took advantage of these properties to develop three new reactions, 1) asymmetric synthesis of chiral quaternary carbon centers, 2) asymmetric synthesis using acetal functions, and 3) organic chemistry using acetal-type reactive salt chemical species, and applied them to biologically active natural products synthesis. New reactions described here are all innovative and useful for natural products synthesis. In particular, the first asymmetric synthesis of fredericamycin A, and concise asymmetric synthesis of anthracycline antibiotics, scyphostatin, ()-Sch 642305, ()-stenine, clavolonine, ()-rubrenolide, ()-rubrynolide, ()-centrolobine, and decytospolide A and B, etc., are noteworthy. Furthermore, since reactions using acetaltype reactive salt chemical species allow the coexistence of functional groups that normally cannot coexist, the reactions using reactive salts have potential to change the retrosynthesis planned based on conventional reactions.

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Section: Intramolecular Haloetherification Of Ene Acetalsmentioning

confidence: 99%