Batzelladine C (3) is a tricyclic guanidine alkaloid of unknown stereochemistry at one centre as well as unknown absolute stereochemistry. The two possible diastereoisomers of the methyl ester corresponding to this compound have been synthesised, permitting the relative and absolute stereochemistry of this compound to be assigned.

Abstract The synthesis of ω-alkenylallylboronates using a heteroatom tether to join both functional groups is described for the first time. Then, these unprecedented compounds were used in tandem Brønsted acid catalyzed allylboration/ring-closing metathesis (RCM) reaction affording heterocyclic derived alcohols as single diastereoisomers. low enantioselectivity observed asymmetric version chira...

The synthesis of new 3-dithiocarbamic flavonoids has been accomplished by the reaction of the corresponding 2-hydroxyaryl dithiocarbamates with aminals. These flavonoids were obtained as a mixture of diastereoisomers, the anti isomer being the major one. The heterocyclization of these compounds provided novel tricyclic flavonoids bearing a 1,3-dithiolium-2-yl ring fused at the 3,4-carbon positi...

Short and high-yielding syntheses of enantiomerically pure (S)-(+) and (R)-(-)-abscisic acid are described. The syntheses proceed through key intermediates that preferentially recrystallise as single diastereoisomers for each enantiomer. This route allows the preparation of either enantiomer of abscisic acid in ca. 30% overall yield, and as demonstrated, gives access to an enantiomerically pure...

Reaction of chiral ester linked diynes with chlorotris(triphenylphosphine)cobalt(I) and sodium cyclopentadienide gave (η(5)-cyclopentadienyl)(triphenylphosphine) cobaltacyclopentadiene complexes as single chiral-at-metal diastereoisomers, including a non-racemic example synthesised in three steps from (S)-3-butyn-2-ol.

A concise method for the formation of cyclopyrophosphate of cIDPRE as well as sulfur and selenium-substituted pyrophosphate cIDPRE analogues (P(1)(S)-cIDPRE, P(1)(Se)-cIDPRE, P(2)(S)-cIDPRE and P(2)(Se)-cIDPRE) was reported and one of the P(S)-diastereoisomers, P(1)(S)-cIDPRE-1, is a novel membrane-permeant cADPR antagonist.

A range of new biphenylazepinium salt organocatalysts effective for asymmetric epoxidation has been developed incorporating an additional substituted oxazolidine ring, and providing improved enantiocontrol in alkene epoxidation over the parent structure. Starting from enantiomerically pure aminoalcohols, tetracyclic iminium salts were obtained as single diastereoisomers through an atroposelecti...