Free radical reactions in synthesis. Total synthesis of isoamijiol.

The dolastane carbon framework present in isoamijiol(1) is elaborated from the enamine(5) using seven carbon-carbon bond forming reactions, four of which involve free radical intermediates.     

Benzothiazines in synthesis. Formal synthesis of erogorgiaene

A benzothiazine, readily available in enantiomerically pure form via a completely selective, intramolecular addition of a sulfoximine-stabilized carbanion to an α,β-unsaturated ester, could be converted to a precursor to erogorgiaene in good overall yield.     

Enynones in organic synthesis. III. A novel synthesis of phenols

Enynones are converted to phenols by an acid catalyzed process which can be controlled to give either of two regioisomeric series of products.     

Aminohaloborane in organic synthesis. VI. A simple enantioselective aldol synthesis

A simple asymmetric aldol condensation of acetophenone and benzaldehydes was performed via chiral vinylaminodichloroborane. The enatioselectivity was compared with that by a similar method using magnesium and lithium.     

Benzothiazines in synthesis. Toward the synthesis of pseudopteroxazole

[reaction: see text] The tricyclic benzothiazine 15 was prepared in a straightforward fashion via a completely stereoselective intramolecular Friedel-Crafts alkylation. This compound represents a potential precursor to the antitubercular agent, pseudopteroxazole. Its synthesis proceeded via a completely selective, intramolecular addition of a sulfoximine-stabilized carbanion to an alpha,beta-unsaturated ester, followed by functional group manipulations.     

Amidoalkylation in organic synthesis.1. Total synthesis of isoretronecanol and trachelanthamidine

The title compounds are prepared in five steps from N-2-bromo ethyl succinimide.     

Total synthesis of (+)-pederin. 1. Stereocontrolled synthesis of (+)-benzoylpedamide

(+)-Benzoylpedamide (5), a right half of (+)-pederin (1), was synthesized stereoselectively based on the newly developed method for the synthesis of 1,3-$\text{syn}$-and 1,3-$\text{anti}$-polyols.     

Benzothiazines in synthesis. A total synthesis of pseudopteroxazole

An enantioselective total synthesis of the naturally occurring antitubercular agent pseudopteroxazole is described. The synthesis is organized around the use of a stereoselective, intramolecular addition of a sulfoximine carbanion to an alpha,beta-unsaturated ester to form an enantiomerically pure benzothiazine. Other important processes include a completely stereoselective intramolecular Friedel-Crafts alkylation and a stereoselective and regioselective hydrogenation. [structure: see text]     

Thallium in organic synthesis. 63. A convenient synthesis of aromatic nitriles

Aromatic nitriles are readily formed by heating arylthallium bis(trifluoroacetates) with CuCN in acetonitrile.     

Improved synthesis of o-phosphohomoserine.

O-Phosphohomoserine (PHS) was prepared in an overall yield of 49% by treatment of N-benzyloxycarbonyl-homoserine p-nitrobenzyl ester with diphenylphosphoryl chloride in pyridine, followed by catalytic hydrogenolysis. Both L - and D , L -phosphohomoserine were found to be 100% hydrolyzed by alcaline phosphatase from E. coli.     

Total synthesis of (+)-pederin. 2. Stereocontrolled synthesis of (+)-benzoylselenopederic acid and total synthesis of (+)-pederin

(+)-Benzoylselenopederic acid (1), a left half of (+)-pederin (3), was synthesized stereoselectively based on the Zn(BH₄)₂ reduction and total synthesis of (+)-pederin (3) was accomplished from 1 and the previously synthesized 2.     

Enynones in organic synthesis. II. An electron transfer mediated synthesis of methylenecyclopentenones

The electrocyclizaton of enynones to methylenecyclopentenones is markedly accelerated by phenols and catechols having a low oxidation potential.