In the present study, we describe the photochemical behaviour of 2-mesyloxy phenyl ketones 8 and 12 bearing a cyclopropane moiety in the side-chain. Irradiation of 8 and 12 leads to the corresponding benzoyl spiro[2.2]pentanes as a consequence of an initial gamma-H-shift, subsequent elimination of MsOH (accompanied by a spin-center shift) and cyclization of the resulting 1,3-diradicals. In cont...

The first organocatalytic Michael-cyclization cascade reaction between isothiocyanato oxindoles and unsaturated pyrazolones has been developed. The multicyclic spiro[oxindole/thiobutyrolactam/pyrazolone] core structures containing three contiguous stereogenic centers, including two spiro quaternary centers, were prepared with excellent diastereo- (up to >20 : 1) and enantioselectivities (up to ...

We report an unusual face selective reduction of the exocyclic double bond in the α-methylene-γ-butyrolactone motif of spiro-oxindole systems. The spiro-oxindoles were assembled by an indium metal mediated Barbier-type reaction followed by an acid catalyzed lactonization.

A general and direct strategy for the synthesis of chiral spiro-aziridine oxindoles has been developed via an aza-Corey-Chaykovsky reaction of isatin-derived N-tert-butanesulfinyl ketimines with excellent selectivity (dr = 98:2 to >99:1). The method is explored for the synthesis of chiral 3-substituted spiro-aziridine oxindoles with high (2S,3S)-selectivity over (2S,3R).

Four new nor-spiro-azaphilones, thielavialides A-D (1- 4), a new bis-spiro-azaphilone, thielavialide E (5), together with pestafolide A (6), were isolated from the endophytic fungal strain, Thielavia sp. PA0001, occurring in the healthy leaf tissue of aeroponically grown Physalis alkekengi. The structures and relative configurations of 1-5 were established on the basis of their MS and NMR data....

The title compound, C(27)H(40)O(4), was obtained from the oxidation of (25R)-3b-hydr-oxy-5a-spiro-stan-12-one (Hecogenin) by Jone's reagent. The mol-ecule contains six alicyclic and heterocyclic rings, all trans-fused, among which four six-membered rings adopt similar chair conformations while two five-membered rings assume an envelope conformation.

We have developed a simple methodology to transform cis-syn-cis-triquinane derivative 2 into the diindole based macrocycle 6 involving Fischer indolization and ring-closing metathesis (RCM). Various spiro-polyquinane derivatives have been assembled via RCM as a key step.

background l-tryptophan is an important ingredient in medicines, especially in neuromedicines such as antidepressants. many commercial processes employ various microorganisms with high tryptophan synthase activity to produce l-tryptophan from indole and l-serine, but these processes are very costly due to the costs of precursors, especially l-serine. objectives for this reason, we studied the a...