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An expeditious synthesis of the (5S,6R,11S,14R)-isomer of acremodiol was developed via a convergent route. One of the required building blocks was synthesized earlier via two sequential lipase-catalyzed secondary carbinol acetylations. The other unit was derived from (R)-2,3-cyclohexylideneglyceraldehyde as a chiral template. The bismacrolide skeleton was constructed by an intermolecular esterification reaction under Mitsunobu conditions followed by a ring-closing metathesis of the resultant α,ω-dialkenoic ester. [ABSTRACT FROM AUTHOR]

Abstract: A chemoenzymatic asymmetric synthesis of the title compound was developed by a building-block approach. The key steps of the synthesis were (i) an enantioselective lipase-catalyzed acylation of a secondary alcohol, (ii) an efficient diastereoselective addition of an alkyl-lithium reagent to a glyceraldehyde derivative, (iii) conversion of an epoxide to a one-carbon homologated allylic alcohol via a sulphorane addition, and (iv) a cross metathesis between two chiral allylic alcohols and subsequent functionalization to obtain the ethyl ester of the hydroxy acid unit of the schulzeines. [Copyright &y& Elsevier]

Abstract: A brief and facile synthesis of the title compound has been developed using cyclohexylideneglyceraldehyde as a chiral template. The key steps in the synthesis were: (i) two highly diastereoselective organometallic addition reactions to the aldehyde to furnish the required synthons with the appropriate stereogenic centers, and (ii) their cross metathesis to give the E-olefin geometry of the target compound. [Copyright &y& Elsevier]

Abstract: The first asymmetric synthesis of (6S,13R)-6,13-dihydroxytetradeca-(2E,4E,8E)-trienoate has been developed. The key steps of the synthesis were the use of an efficient lipase-catalyzed acylation, a chiral template-driven enantiocontrolled allylation for introducing the stereogenic centers, and a cross-metathesis for controlling the C-8 olefin geometry. [Copyright &y& Elsevier]

Abstract: A facile chemoenzymatic synthesis of the harzia lactone A enantiomers was developed. A lipase-catalyzed acylation and an enantio-controlled substrate and reagent-controlled Sharpless’ asymmetric dihydroxylation are the key features of the synthesis. [Copyright &y& Elsevier]

Abstract: An asymmetric synthesis of herbarumin III has been developed using (R)-cyclohexylidene glyceraldehyde 1 as the chiral template. The key steps of the synthesis were the enantioselective preparation of the required homoallylic alcohol from 1, an asymmetric dihydroxylation, and a ring-closing metathesis reaction for the macrolactonization. [Copyright &y& Elsevier]

Abstract: A brief and facile synthesis of the title compounds has been developed by using an efficient lipase-catalyzed acylation and a chiral template-directed diastereoselective alkylation for incorporating the stereogenic centres. A cross-metathesis was employed to get the required E-olefin geometry. [Copyright &y& Elsevier]

Abstract: A facile synthesis of sulfobacin A has been developed starting from (R)-cyclohexylideneglyceraldehyde (11). The key steps in the synthesis are the highly diastereocontrolled allylation of 11 and syn-selective reduction of a ketone derived from 11. The other attractive features are the operational simplicity and the use of inexpensive compounds/reagents. [Copyright &y& Elsevier]

An asymmetric synthesis of a 3′-deoxy-3′- 18 F-fluorothymidine ( 18 F-FLT) precursor has been developed wherein the deoxysugar moiety was synthesized using a novel Ga-mediated allylation of ( R )-2,3-cyclohexylideneglyceraldehyde as the key step. The synthesis deviates significantly from the previous syntheses of the 18 F-FLT precursors wherein the expensive starting material, thymidine was used. [ABSTRACT FROM AUTHOR]

An efficient asymmetric synthesis of the C 22 -trihydroxy fatty acid component of macroviracin A has been developed. The key steps were highly enantioselective (i) lipase-catalyzed acylation, (ii) InCl 3 -( S )-BINOL mediated allylation, and (iii) asymmetric dihydroxylation (ADH) reaction. The moderate diastereoselectivity of the ADH reaction was overridden by converting the resultant diol diastereomers to the required epoxide enantiomer. [ABSTRACT FROM AUTHOR]

Abstract: A chemoenzymatic asymmetric synthesis of the title compound has been developed using an efficient lipase-catalyzed acylation and a chiral reagent-directed diastereoselective allylation as the key steps for incorporating the stereogenic centers. A cross metathesis was employed to obtain the required E-olefin geometry of the target compound. [Copyright &y& Elsevier]

Abstract: A facile asymmetric synthesis of the octalactin lactone was developed staring from (R)-cyclohexylideneglyceraldehyde (1). The key step of the synthesis is an In-mediated diastereoselective crotylation of 1 in water, which furnished the building blocks with the required stereochemistry under operationally simple conditions. Their conversion to the appropriate intermediates, invertive esterification and a ring closing metathesis reaction furnished the target compound. [Copyright &y& Elsevier]

Abstract: An innovative and facile synthesis of the title compound has been developed starting from (R)-cyclohexylidene glyceraldehyde. The key step in the synthesis is a chiral template-driven Grignard addition with absolute diastereocontrol. The other attractive features are the operational simplicity and the use of inexpensive compounds/reagents. [Copyright &y& Elsevier]