Hidekazu Takeno

Total synthesis of (+)-castanospermine from D-mannose

Abstract A total synthesis of (+)-castanospermine (2) has been achieved starting from D-mannose by a route adopting a double-cyclization process (5c→6) as the key step.

Studies on phosphonic acid antibiotics. I. Structure and synthesis of 3-(n-acetyl-n-hydroxyamino)propylphosphonic acid (FR-900098) and its n-formyl analogue (FR-31564)

Abstract The structure elucidation of FR-900098 ( 1 ) isolated from a microorganism source and the syntheses of FR-900098 and its N-formyl analogue, FR-31564 ( 2 ), are described. The latter possesses a superior antimicrobial activity.

Studies on phosphonic acid antibiotics. II. Synthesis of 3-(n-acetyl-n-hydroxyamino)-2(r)-hydroxypropylphosphonic acid (FR-33289) and 3-(n-formyl-n-hydroxyamino)-1-trans-propenylphosphonic acid (FR-32863)

The syntheses of FR-33289 (3), originally isolated from a microorganism, and FR-32863 (6), first designed on the basis of a biogenetic consideration and recently found to be also present in nature, are described.

An efficient method for selective amino acid protection of meso-2,2′-diaminodicarboxylic acid: An improved synthesis of FK-156

Abstract An efficient method for selective amino acid protection with proper differentiation between the two amino acid groups in meso-2,2′-diaminopimelic acid has been achieved [ 7 → 8 → 9 → 10 → 11 ] and applied to the synthesis of FK-156 [ 10 → 12 → 14 → 1 ].

Synthesis of demethoxycapillarisin, a naturally occurring 2-phenoxychromone, and related compounds

Demethoxycapillarisin (1), a naturally occurring 2-phenoxychromone, and the related compounds (2)–(4) have been synthesized via a route involving, as a key step, an intramolecular Wittig reaction between a phosphorus ylide and a carbonate.

Novel synthesis of 3-alkyl-2-phenoxychromones involving an intramolecular Wittig reaction of carbonates

The intramolecular Wittig reaction between phosphorus ylides and carbonates provides a simple, convenient method for preparing cyclic keten-acetal structures.