Fertility restoration in mice with chemotherapy induced ovarian failure using differentiated iPSCs.

Background: Treatment options for premature ovarian insufficiency (POI) are limited to hormone replacement and donor oocytes. A novel induced pluripotent stem cell (iPSC) transplant paradigm in a mouse model has potential translational applications for management of POI.

Methods: Mouse ovarian granulosa cell derived-iPSCS were labelled with green fluorescent protein (GFP) reporter and differentiated in vitro into oocytes.

A Translational Model to Improve Early Detection of Epithelial Ovarian Cancers.

Neural network analyses of circulating miRNAs have shown potential as non-invasive screening tests for ovarian cancer. A clinically useful test would detect occult disease when complete cytoreduction is most feasible. Here we used murine xenografts to sensitize a neural network model to detect low volume disease and applied the model to sera from 75 early-stage ovarian cancer cases age-matched to 200 benign adnexal masses or healthy controls.

Simple strategy for synthesis of optically active allylic alcohols and amines by using enantioselective organocatalysis.

A simple organocatalytic one-pot protocol for the construction of optically active allylic alcohols and amines using readily available reactants and catalyst is presented. The described reaction is enabled by an enantioselective enone epoxidation/aziridination-Wharton-reaction sequence affording two highly privileged and synthetically important classes of compounds in an easy and benign way. The advantages of the described sequence include easy generation of stereogenic allylic centers, also including quaternary stereocenters, with excellent enantio- and diastereomeric-control and high product diversity.

An unexpected Michael-aldol-smiles rearrangement sequence for the synthesis of versatile optically active bicyclic structures by using asymmetric organocatalysis.

A facile and simple organocatalytic procedure to generate optically active 6-alkyl- and 6-aryl-substituted bicyclo[2.2.2]oct-5-en-2-ones is presented.

Asymmetric organocatalysis with sulfones.

Asymmetric organocatalysis has become a powerful tool for the synthesis of optically active compounds. Whereas early research mainly focused on combining simple reagents as a proof-of-concept for asymmetric organocatalysis, recent investigations are directed towards extending the concept to more target- and diversity-oriented synthesis. As a result of the many transformation possibilities and their ability to generate both nucleophilic and electrophilic reaction partners, sulfones have become especially important substrates in the field of organocatalysis.

Asymmetric organocatalytic formal alkynylation and alkenylation of alpha,beta-unsaturated aldehydes.

A highly stereoselective organocatalytic one-pot protocol for the formal alkynylation and alkenylation of alpha,beta-unsaturated aldehydes using novel chemistry based on beta-keto heterocyclic sulfones is presented. The organocatalytic step is catalyzed by a prolinol derivative and allows for the formation of important optically active compounds. Further transformations of the beta-keto heterocyclic sulfone moiety, based on new developments of the Smiles rearrangement through a process parallel to the Julia-Kocienski reaction, were performed leading to beta-alkynylated aldehydes and 3-alkenylated alcohols.

Ring-rearrangement metathesis.

Ring-rearrangement metathesis (RRM) refers to the combination of several metathesis transformations into a domino process, in which an endocyclic double bond of a cycloolefin reacts with an exocyclic alkene. RRM has proven to be a powerful method for the rapid construction of complex structures. The extension of the basic ring-opening-ring-closing metathesis process by further metathesis steps as well as an examination of the driving forces, limits, scope, recent advantages, and future perspectives of these domino sequences is presented with various examples, thus reflecting the high efficiency and utility of RRM in organic synthesis.

Total synthesis of (+)-trans-195A.

[reaction: see text] The first enantioselective synthesis of (+)-trans-195A is described. The structure has been constructed by ring-rearrangement metathesis (RRM) and zirconium-mediated Negishi-coupling, used for the first time to prepare 6,6-membered heterocycles, as key steps. By comparison of the synthesized material with the isolated natural product, the absolute configuration of natural trans-195A was determined to be (2R,4aS,5R,8aS)-(-).