Biocatalytic Approach for the Total Synthesis of (–)‐Malyngolide and Its C(5)‐Epimer

An enzymatic approach has been successfully utilized in the total synthesis of (–)-malyngolide and its C(5)-epimer. The required configuration was established by an enzymatic kinetic resolution and Sharpless asymmetric dihydroxylation.

[1]  M. H. Fernandes,et al.  Marine Cyanobacteria Compounds with Anticancer Properties: A Review on the Implication of Apoptosis , 2012, Marine drugs.

[2]  J. Yadav,et al.  The stereoselective total synthesis of (−)-cleistenolide , 2011 .

[3]  D. Matulis,et al.  Probing the influence of an allylic methyl group in zearalenone analogues on binding to Hsp90. , 2010, Chemistry.

[4]  W. Gerwick,et al.  Malyngolide dimer, a bioactive symmetric cyclodepside from the panamanian marine cyanobacterium Lyngbya majuscula. , 2010, Journal of natural products.

[5]  B. Trost,et al.  Asymmetric synthesis of quaternary centers. Total synthesis of (-)-malyngolide. , 2000, Organic letters.

[6]  D. Doren,et al.  Cyclohexenone Construction by Intramolecular Alkylidene C−H Insertion: Synthesis of (+)-Cassiol , 1996 .

[7]  Jens Hartung,et al.  The Osmium-Catalyzed Asymmetric Dihydroxylation: A New Ligand Class and a Process Improvement , 1992 .

[8]  E. Santaniello,et al.  Enantioselective transesterification of 2-methyl-1,3-propanediol derivatives catalyzed by pseudomonas fluorescens lipase in an organic solvent , 1992 .

[9]  B. Giese,et al.  Total Synthesis of (−)‐Malyngolide and of Its Three Stereomers , 1987 .

[10]  Jeffery T. Davis,et al.  Horner-wadsworth-emmons reaction: Use of lithium chloride and an amine for base-sensitive compounds , 1984 .

[11]  R. Wade Catalyzed reduction of organofunctional groups with sodium borohydride , 1983 .

[12]  P. Rollin,et al.  A synthesis of the marine antibiotic (-)-malyngolide from D-glucose , 1983 .

[13]  T. Mukaiyama,et al.  AN ASYMMETRIC TOTAL SYNTHESIS OF A NEW MARINE ANTIBIOTIC-MALYNGOLIDE , 1980 .

[14]  Richard E. Moore,et al.  Structure and absolute configuration of malyngolide, an antibiotic from the marine blue-green alga Lyngbya majuscula Gomont , 1980 .

[15]  A. Mancuso,et al.  Oxidation of long-chain and related alcohols to carbonyls by dimethyl sulfoxide "activated" by oxalyl chloride , 1978 .