Ae. de Groot

A novel synthesis of α-sulfenylated aldehydes

Abstract Ketones are converted into α-sulfenylated aldehydes with addition of one carbon atom via reaction with methoxyphenylthiomethyllithium followed by rearrangement of the adducts.

Investigations into the total synthesis of insect antifeedant clerodanes the total synthesis of ± 4-epi ajugarin

Abstract Starting from alcohol 3 , a stereospecific synthesis of carboxylic acid 2 is described. This acid 2 is a key intermediate in the total synthesis of ajugarins and its conversion into ± 4-epi ajugarin is reported.

The total synthesis of (±)-colorata-4(13), 8-dienolide

Abstract The total synthesis of (±)-colorata-4(13),8-dienolide ( 1 ), a sesquiterpene with a rearranged drimane skieleton, is described using 6β, 8aβ-dimethyl-5-methylene-3,4,4aα, 5,6,7,8,8a-octahydro-1(2H)-naphtalenone ( 10 ) as a key intermediate. A new annelation method for butenolides via hydrolysis of a thiohenyl furan is reported.

Functionalized dienes via thermolysis of allylic sulfoxides

Abstract Thermolysis of allylic sulfoxides is a useful method for the synthesis of functionalized dienes.

A selective base-induced rearrangement of perhydronaphthalenes to 1,5-cis-fused 10-methylene perhydroazulenes.

Abstract The rearrangement of perhydronaphthalenic tosylate 3 to 1,5- cis 10-methylene perhydroazulene 4 was achieved selectively and in high yield via intramolecular assistance of a 4β hydroxylate.

Stereospecific formation of a substituted trans-decaline as an intermediate for the synthesis of clerodane insect antifeedants

The stereospecific synthesis of trans-decaline 3† is described. This compound is an important intermediate in the total synthesis of Clerodane insect antifeedants, as exemplified by ajugarin-I.

Preparation and reactions of cis-5,10-methanoxymethano-1-methyl-Δ1,9-2-octalone as an intermediate in the total synthesis of clerodane type diterpenes

The synthesis of cis-5,10-methanoxymethano-1-methyl-Δ1,9-2-octalone (5) is described. Its value as an intermediate is demonstrated by a number of reactions that are essential in the planned total synthesis of clerodane diterpenes.

Stereospecific preparation of (±)-4,4-dinor-9βH-pimara-7,15-diene, a model for the total synthesis of momilactone type diterpenes

Abstract The synthesis of (±)-4,4-dinor-9βH-pimara-7,15-diene, 4, a model compound for momilactones, has been achieved via stereospecific Diels-Alder reaction and alkylation.

The preparation of (±) 18,19-epoxy-14,15,16-trisnorclerodan-13-oic acid as a key intermediate in the total synthesis of clerodane type diterpenes

Abstract The stereospecific preparation of (±) 18,19-epoxy-14,15,16-trisnorclerodan-13-oic acid is described. This compound can serve as a key intermediate in the preparation of clerodane diterpenes as it possesses the right stereochemistry at all asymmetric centres.