Chinh Thien Bui

Structure-guided rescaffolding of selective antagonists of BCL-XL

Because of the promise of BCL-2 antagonists in combating chronic lymphocytic leukemia (CLL) and non-Hodgkins lymphoma (NHL), interest in additional selective antagonists of antiapoptotic proteins has grown. Beginning with a series of selective, potent BCL-XL antagonists containing an undesirable hydrazone functionality, in silico design and X-ray crystallography were utilized to develop alternative scaffolds that retained the selectivity and potency of the starting compounds.

Constructing the side-chain of the polyketide herbicide herboxidiene: aprotocol for the synthesis of enantiomerically enriched C-11 to C-19fragments

The aldehyde 5, corresponding to the C-11 to C-19 fragment of the polyketide herbicide herboxidiene 1, has been prepared in enantio-enriched form.

One-Pot Microwave-Assisted Synthesis of 3,4-Disubstituted 2-Quinolinones

Abstract An improved one-pot synthesis of 3,4-disubstituted 2-quinolinones is described. The condensation of substituted 2-aminobenzophenone (or 2-aminophenyl alkyl ketone) with acid chlorides was carried out in the presence of triethylamine (or NaH) under microwave reaction conditions (150oC, 200 psi). The reactions were completed within minutes to produce 2-quinolinones in moderate to excellent yields and good purities. [Supplementary materials are available for this article. Go to the publishers online edition of Synthetic Communications® for the following free supplemental resource(s): Full experimental and spectral details.] GRAPHICAL ABSTRACT

Diastereoselective synthesis of the tetrahydropyranoid core of the polyketide herbicide herboxidiene and model studies pertaining to attachment of the side-chain

A diastereoselective synthesis of compound 2, which embodies the tetrahydropyranyl core of the polyketide herbicide herboxidiene (1), has been developed using asymmetric epoxidation of nerol as the initial step. Ketone 2 has been elaborated to phosphine oxide 24 which engages in a Horner–Wittig reaction with nonanal to give the E,E-diene 27, an analogue of herboxidiene. However, unlike compound 1, congeners 2 and 27 are not phytotoxic.

Diastereoselective route to the tetrahydropyranoid core of the polyketide herbicide herboxidiene

Nerol 15 is readily converted,via initial asymmetric epoxidation, into compound 2 which contains the tetrahydropyranoid core of herboxidiene 1, a potent phytotoxic compound isolated from Streptomyces sp. A7847.