Total Synthesis and Structural Confirmation of Chlorodysinosin A  [J. Am. Chem. Soc.2006,128, 10491−10495].

Abstract

References(1) For recent reviews on cyanobacterial metabolites, see: (a) Burja Angew. Chem., Int. Ed. 1998, 37, 2162 Matsunaga, S. Chem. ReV. 1993, 93, 1783

Heterogenisation of a C‐Scorpionate FeII Complex on Carbon Materials for Cyclohexane Oxidation with Hydrogen Peroxide

“…Our interest in the azido ring‐opened products lies in the remarkable advantages that this functional group presents compared with the corresponding amino ring‐opened products, such as the ease of handling over their amino counterparts and, in addition, the possibility of being readily transformed into the corresponding aziridines, which are interesting and useful building blocks 4. Thus, when azido alcohols 23a , 25a and 27a were treated with Ph 3 P,15 aziridines 28 , 29 and 30 were efficiently obtained in yields of 62, 92 and 89 %, respectively. Interestingly, when a mixture of azido alcohols, such as 23a / 23b , was used, only one aziridine ( 28 ) was obtained.…”

A straightforward route to enantiopure α-substituted derivatives of (2S,3aS,7aS)-octahydroindole-2-carboxylic acid

“…In the context of functionalized Oic derivatives, synthetic effort has been primarily oriented to the preparation of 6-substituted 2-carboxy octahydroindoles7b–e because they constitute the core subunit of a family of marine metabolites (aeruginosins) with activity as protease inhibitors. Besides this substitution pattern, α-substituted Oic derivatives7a are very attractive scaffolds as they are the core structure of compounds with anti-arthritic activity.…”

“…Besides this substitution pattern, α-substituted Oic derivatives7a are very attractive scaffolds as they are the core structure of compounds with anti-arthritic activity. Even more importantly, as α-substituted proline analogues,8 they are of high intrinsic value in the design of modified peptides.…”

“…However, despite their potential value, the preparation of α-tetrasubstituted Oic analogues remains almost unexplored 7a,10. This observation has stimulated our interest in developing efficient routes to produce the different stereoisomers of α-substituted octahydroindole-2-carboxylic acids in enantiomerically pure form—in particular, those with a cis-fused bicyclic structure.…”

Efficient access to enantiomerically pure cyclic α-amino esters through a lipase-catalyzed kinetic resolution

“…For example, it is present in marine compounds with antithrombotic properties;9 in the dipeptide perindropil (a potent antihypertensive drug used in the prevention of cardiovascular disorders such as heart failure);10 and in the prolyl oligopeptidase inhibitor S 17092, a compound with antiamnesic and cognitive-enhancing properties 11. Recently, some of us reported12 the synthesis of enantiomerically pure (2 S ,3a S ,7a S )- and (2 R ,3a R ,7a R )-Oic derivatives using preparative chiral HPLC,12a and that of the (2 R ,3a S ,7a S ) isomer by selective formation of a trichloromethyloxazolidinone 12b.…”