Yoshinori Sekiguchi

Practical synthesis of (R)-γ-amino-β-hydroxybutanoic acid (GABOB) from (R)-epichlorohydrin

Abstract (R)-Epichlorohydrin has efficiently been converted to the hypotensive and antiepileptic compound, (R)-γ-amino-β-hydroxybutanoic acid (GABOB), in six steps in 57% overall yield.

Stereochemistry of the proposed intermediates in the biosynthesis of mycinamicins

Abstract Stereochemistry of the proposed intermediates in the biosynthesis of mycinamicins isolated from the culture filtrate of Micromonospora griserubida sp. has been established.

Concurrent reductive cleavage and recombination of γ,δ-alkylidenedioxy-α,β-unsaturated esters promoted by organocuprates

Treatment of γ,β-alkylidenedioxy-α,β-unsaturated esters (1) with lithium dimethylcuprate furnishes β′δ-dihydroxy-β,γ-unsaturated esters (2) in moderate to good yields by concurrent reductive cleavage to ketones (5) and enolates (6) and their aldolic recombination.

Enantiocontrolled synthesis of the C9-27 segment of milbemycin K from (R)- and (S)-epichlorohydrins

The C 9-27 segment (11) of milbemycin K (10) has been synthesized using two molar equivalents of (R)-epichlorohydrin [(R)-1] and one molar equivalent of (S)-epichlorohydrin [(S)-1] as chiral building blocks

An enantiocontrolled route to protomycinolide IV and its presumed biogenetic precursors using (S)-O-benzylglycidol

Starting with (S)-O-benzylglycidol (9) as only chiral building block, a formal synthesis of protomycinolide IV (1) and the first syntheses of its presumed biogenetic precursors methyl epimycinonate I (2), methyl mycinonate I (3), methyl mycinonate II (4), and decarboxymycinonic acid III (5), have been achieved via the eight-carbon unit (8) as a common intermediate

An enantiocontrolled route to the C11-17 segment of mycinamicins III and IV

An enantiocontrolled route to the common C 1 1 -17 segment (2) of mycinamicins III (1a) and IV (1b) has been developed starting from the chiral α-hydroxyacetylene (6) obtained from (E)-4-benzyloxybut-2-en-1-ol (3)

Versatile chiral building blocks bearing a secondary methyl group from (S)-O-benzylglycidol (benzyloxymethyloxirane)

Versatile chiral building blocks for the construction of chiral natural products bearing a secondary methyl group have been efficiently prepared from (S)-O-benzylglycidol.