Susumi Hatakeyama

A new route to substituted 3-methoxycarbonyldihydropyrans; enantioselective synthesis of (–)-methyl elenolate

A stereoselective chiral synthesis of (–)-methyl elenolate has been achieved by employing a newly developed method for the construction of substituted 3-methoxycarbonyldihydropyrans based on a radical cyclisation reaction.

An efficient route to a key A-ring synthon for 1α,25-dihydroxyvitamin D3 and its analogs

Abstract An efficient and highly stereoselective route to the Roches A-ring synthon of 1α,25-dihydroxyvitamin D 3 from R -(−)-epichlorohydrin has been developed utilizing double propargylation of R -(−)-epichlorohydrin and palladium(O) catalyzed intramolecular Heck type of reaction of the ω-vinyl-(Z)-iodoalkene as key steps.

Preparation of (2R,3S)-1,2-epoxypent-4-en-3-ol, a new chiral building block for the synthesis of (+)-endo- and (–)-exo-brevicomin

Asymmetric epoxidation of the divinylcarbinol (7) using L-(+)-diethyl tartrate gave (2R,3S)-1,2-epoxypent-4-en-3-ol (8), which was utilized as a chiral building block in the synthesis of (+)-endo- and (–)-exo-brevicomin.

Total Synthesis of Oxazolomycin A

The first total synthesis of oxazolomycin A, a structurally novel oxazole polyene γ-lactam/β-lactone antibiotic, is described. Key features include the stereocontrolled construction of the right-hand heterocyclic core by taking advantage of an In(III)-catalyzed Conia-ene type cyclization and the asymmetric synthesis of the left-hand segment starting with a Cinchona alkaloid-catalyzed cyclocondensation of an aldehyde with an acid chloride.

Efficient ester exchange reaction of phosphonoacetates

Abstract A novel method for the preparation of differentially substituted phosphonoacetates and phosphonoacetamides using 4-DMAP catalyzed ester exchange reaction has been developed.

Asymmetric Total Synthesis of (+)-Phoslactomycin B

(+)-Phoslactomycin B was synthesized by a highly enantio- and stereoselective approach involving asymmetric pentenylation, Suzuki-Miyaura coupling, ring-closing metathesis, asymmetric dihydroxylation, and Stille coupling. The synthetic method developed enables us to synthesize three other isomers concerning the C11-OH and Delta12-double bond.

Enantioselective synthesis of (+)-citreoviral using asymmetric hydroxylation of tiglate esters

Abstract A microbial metabolise (+)-citreoviral has been synthesized enantio-and stereo-selectively using newly developed asymmetric hydroxylation of tiglate esters for the construction of the key chiral building block.

A novel enantioselective synthesis of (+)-myriocin based on the chemistry of 1-trimethylsilylbuta-2,3-dienes

Abstract A synthesis of (+)-myriocin has been achieved in a highly stereoselective manner employing TiCl 4 catalyzed addition of 1-trimethylsilylbuta-2,3-diene to an aldehyde and Et 2 AlCl catalysed cyclization of an epoxytrichloroacetimidate for the construction of its α-substituted serine structure having three contiguous asymmetric centers.

Versatile enantiocontrolled synthesis of (+)-fostriecinElectronic supplementary information (ESI) available: experimental section. See http://www.rsc.org/suppdata/cc/b2/b209742g/

Fostriecin, a potent protein phosphatase inhibitor and antitumor agent, has been enantioselectively synthesized in naturally occurring form via a versatile route, which also allows one to secure all possible stereoisomeres of the C1-C13 fragment including the C11 stereocenter and the geometry of the delta 12-double bond.

Synthesis of viridiofungin A trimethyl ester and determination of the absolute structure of viridiofungin A

Abstract Four diastereoisomeric trimethyl esters of viridiofungin A, a member of novel family of aminoacyl alkyl citrate compounds, were synthesized in a highly stereoselective manner and the absolute configuration of natural viridiofungin A was determined to be 3 S ,4 S ,2′ S .