Studies directed towards the synthesis of immunosuppressive agent FK 506 : Synthesis of C-20 to C-27 moiety

Rao, A. V. Rama; Chakraborty, Tushar Kanti; Purandare, A. V.

doi:10.1016/s0040-4039(00)88828-0

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Cited by 15 publications

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“…The present work is the first protocol of this type of transformation except for organocopper reagents. Although the reactions of epoxy alcohols 4 and 5 with dimethylcupurate have been widely used in the synthesis of various natural products, e.g., tautomycin, ingramycin, olygomycin, rodularin, FK-506, etc., their stereoselectivity and chemical yields were not always satisfactory. Therefore, this new methodology provides an extremely useful tool for natural product synthesis.…”

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confidence: 99%

Regioselective Alkyl and Alkynyl Substitution Reactions of Epoxy Alcohols by the Use of Organoaluminum Ate Complexes: Regiochemical Reversal of Nucleophilic Substitution Reactions

Sasaki

Tanino²,

Miyashita³

2001

Org. Lett.

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Unprecedented nucleophilic substitution reactions of 2,3-epoxy-1-alkanols with alkyl- and alkynylaluminum ate complexes have been studied and demonstrated to occur at the C2 position with extremely high stereoselectivity, i.e., with exactly reversed regioselectivity to that obtained in the substitution reactions by normal organoaluminum reagents, resulting in the formation of the C2-alkyl and C2-alkynyl substitution products in excellent yields.

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confidence: 99%