Jianhua Ye

Stereospecific α-alkoxystannane couplings with acyl chlorides: Total synthesis of (+)-goniofufurone

Abstract Stereospecific C-glycoside formation via Pd/Cu mediated coupling of PhCOCl with cyclic α-alkoxystannane 6 , derived from D -glucurono-6,3-lactone, was the key transformation in a concise total synthesis of the anticancer agent (+)-goniofufurone.

Chiral cyclopropanes: asymmetric synthesis of constanolactones A and B

Abstract The title marine eicosanoids were prepared using a novel, stereoselective bis-annulation to create the characteristic cyclopropane-δ-lactone motif.

A preparation of benzylic and allylic boronates: Cross-coupling of aryl- and alkenylstannanes with bromomethylboronates

Abstract Palladium catalyzed cross-coupling of aryl- or alkenylstannanes with pinacol and pinanediol bromomethylboronates affords the corresponding homologated benzylic or allylic boronates in moderate to good yields.

Conjugate addition of α-alkoxystannanes via in situ transmetalation using catalytic CuCN

Abstract Catalytic CuCN mediates the in situ transrnetalation of α-thionocarbamoyl stannanes and subsequent conjugate addition to α,β-unsaturated carbonyls in the presence of chlorotrimethlysilane at or a little above room temperature.

Convenient preparation of α-trimethylsilyloxy- and α-hydroxystannanes from aldehydes

Abstract Aldehydes, but not ketones, are converted to α-hydroxystannanes via the corresponding silyl ethers in good to excellent yields by Bu4NCN catalyzed addition of Bu3SnSiMe3 and hydrolytic isolation. Modest asymmetric induction was observed using a chiral quaternary ammonium cyanide catalyst.

GPI membrane anchors: synthesis and functional evaluation of aminoglucosyl phosphatidylinositol core analogs

Abstract Analogs of GPI membrane anchor precursors were prepared from chiral inositol 1 and evaluated as substrates in rodent and trypanosomal cell-free incubates. Di-octanoyl GlcNα-PI 5b was an efficient mannose acceptor whereas di-palmitoyl GlcNα-PI 5a was unexpectedly refractory. Di-octanoyl β-anomer 8 was mannosylated only under conditions that permitted acylation of the inositol residue.

Intracellular second messengers: Synthesis of L-α-phosphatidyl-D-myo-inositol 3,4-bisphosphate and analogs

Abstract Concise syntheses of the title phospholipid as well as a water soluble, short chain diester and a cross-linkable aminodiether analog utilized chiral inositol 1 .