Stereoselective Formal Total Synthesis of (-)-Didemniserinolipid B

A formal total synthesis of (-)-didemniserinolipid B from L-(+)-tartaric acid is presented. Key features of the synthesis include construction of the bicyclic acetal core from bisdimethyl amide of tartaric acid and further elaboration by cross metathesis.

An expeditious enantiospecific total synthesis of (+)-7-epi-goniofufurone

Stereoselective synthesis of styryl lactone, (+)-7-epi-goniofufurone was achieved in high yield via simple transformations from tartaric acid. The key step involves the successive stereoselective reduction of ketones with borohydride and selectride.

Facile enantiospecific synthesis of (+)-iso-cladospolide B

Enantiospecific synthesis of bio-active butenolide (+)-iso-cladospolide B from D-(-)-tartaric acid in a short synthetic sequence is presented. Pivotal reaction sequence includes cross metathesis of an alkene and Wittig olefination. (C) 2010 Elsevier Ltd. All rights reserved.

Stereoselective synthesis of cytotoxic anhydrophytosphingosine pachastrissamine [Jaspine B]

A practical stereoselective synthesis of cytotoxic anhydrophytosphingosine pachastrissamine (jaspine B) was achieved in 48% overall yield from D-(-)-tartaric acid. Key features of the sequence include the diastereoselective formation of a tetrol with three contiguous chiral centers, which was further elaborated to pachastrissamine. The synthetic route is operationally simple, diastereoselective and is amenable for the synthesis of a number of analogues of pachastrissamine.

Enantiospecific total synthesis of (+)-lentiginosine

A facile synthesis of (+)-lentiginosine is accomplished from L-(+)-tartaric acid. Key transformations in the synthesis include the elaboration of gamma-oxo amide derived from tartaric acid.

Formal total synthesis of (+)-didemniserinolipid B

The formal total synthesis of (+)-didemniserinolipid B, a marine tunicate possessing a 6,8-dioxabicyclo3.2.1]octane framework, was accomplished starting from L-(+)-tartaric acid. The key transformations in the synthesis include the elaboration of a gamma-hydroxy-amide readily obtained by desymmetrization of tartaric acid bis-amide via the controlled addition of a Grignard reagent followed by stereoselective reduction of the resulting ketone. (C) 2010 Elsevier Ltd. All rights reserved.

Stereoselective total synthesis of (+)-synargentolide A

The stereoselective synthesis of synargentolide A, a polyhydroxy delta-lactone, has been accomplished from tartaric acid. The key steps in the synthesis involve Keck and Brown allylations and ring closing metathesis. (C) 2010 Elsevier Ltd. All rights reserved.

Total Synthesis of Gabosine H

Stereoselective total synthesis and assignment of the absolute configuration of the keto carba sugar gabosine H is presented. Pivotal reactions in the sequence include desymmetrization of the dimethylamide of tartaric acid and ring-closing metathesis.

Synthesis and Degradation of Sorbitol-Based Polymers

A new class of biodegradable copolyesters was synthesized by the catalyst-free melt condensation of sorbitol with citric acid, tartaric acid, and sebacic acid. The resulting polymers were designated as poly(sorbitol citric sebacate) p(SCS)] and poly(sorbitol tartaric sebacate) p(STS)]. The synthesized polymers were characterized by Fourier transform infrared spectroscopy, H-1-NMR spectroscopy, and differential scanning calorimetry analysis. Porous spongelike scaffolds were prepared with a salt-leaching technique and characterized with scanning electron microscopy. Tensile testing of the p(SCS) and p(STS) polymers showed that they exhibited a wide range of mechanical properties. The Young's modulus and tensile strengths of the polymers ranged from 1.06 +/- 0.12 to 462.65 +/- 34.21 MPa and from 0.45 +/- 0.04 to 20.32 +/- 2.54 MPa, respectively. In vitro degradation studies were performed on disc-shaped polymer samples. The half-life of the polymers ranged from 0.54 to 38.52 days. The percentage hydration of the polymers was in the range 9.36 +/- 1.26 to 78.25 +/- 1.91, with sol contents of 2-14%. At any given polymer composition, the Young's modulus and tensile strength of p(SCS) was higher than that of p(STS), whereas the degradation rates of p(SCS) was lower than that of p(STS). This was attributed to the structural difference between the citric and tartaric monomers and to the degree of crosslinking. (C) 2011 Wiley Periodicals, Inc. J Appl Polym Sci 121: 2861-2869, 2011

Total Synthesis of (-)-Anamarine

Total synthesis of polyhydroxy delta-pyranone natural product (-)-anamarine is accomplished from D-(-)-tartaric acid. The main feature of the synthesis is the utility of hitherto unexplored beta-keto phosphonate derived from tartaric acid amide and further elaboration involving stereoselective reduction.

Total synthesis of panaxytriol and panaxydiol

The enantioselective total synthesis of the diyne containing natural products panaxytriol and (3S,10R)-panaxydiol from L-tartaric acid is reported. Key steps in the synthesis include the elaboration of a gamma-hydroxy amide derived from tartaric acid to the required alkyne and the formation of the desired diyne unit by a Cadiot-Chodkiewicz coupling. (C) 2011 Elsevier Ltd. All rights reserved.

Excellent chirality transcription in two-component photochromic organogels assembled through J-aggregation

Organogels made of pyridine-end oligo-p-phenylenevinylenes with tartaric acid exhibit remarkable J-aggregation induced red-shifts (Dk = 55 nm) and notable chirality transcription. Induction of liquid-crystalline behavior is also tuned in the supramolecular assembly.

Enantiospecific Total Synthesis of (-)-Bengamide E

Total synthesis of the polyhydroxy caprolactam amide natural product, bengamide E, is accomplished starting from tartaric acid. Key reactions in the synthesis include desymmetrization of the bis(dimethylamide) unit of tartaric acid, Zn(BH4)2-mediated anti-selective reduction, and a HornerWadsworthEmmons olefination.

An Expeditious Enantiospecific Total Synthesis of (-)-Crassalactone C

A concise and expeditious approach for the total synthesis of bioactive styryllactone (-)-crassalactone C is presented from tartaric acid. The main features of the synthesis include the desymmetrization of dimethylamide of tartaric acid and the effective use of cinnamoyl ester as a protecting group as well as a reactant in the ring-closing metathesis reaction.

Unprecedented formation of a 14-membered dihydropyran macrocycle via sequential olefin cross metathesis-intramolecular hetero Diels-Alder reaction

Formation of a 2,3-dihydro-4H-pyran containing 14-membered macrocycle by sequential olefin cross metathesis and a highly regiospecific hetero Diels-Alder reaction was observed in the reaction of a hydroxydienone derived from tartaric acid with Grubbs' second generation catalyst. It was found that the free alcohol in the hydroxyenone led to the macrocycle formation, while protection of the hydroxy group formed the ring closing metathesis product. (C) 2013 Elsevier Ltd. All rights reserved.