Giovanni Palmisano

(-)-β-Pinene as chiral promoter. Stereospecific access to (-)-γ-amino-β(r)-hydroxybutyric acid (gabob) and (r)-carnitine.2

Abstract The stereochemical correlation between the ene adducts 2 and 4a and their products of alkaline hydrolysis is reported. Starting from 2, by using a degradative sequence, a stereocontrolled approach to γ-amino-β( R )-hydroxybutyric acid (GABOB) 8f and ( R )-carnitine hydrochloride 8g is described.

Lipase-mediated resolution of 2-cyclohexen-1-ols as chiral buildingblocks en route to eburnane alkaloids

Abstract Lipase catalyzed esterification of several 2-cyclohexen-1-ols proceeds with excellent enantioselectivity leading to ( S )-enantiomers as promising chiral building blocks en route to eburnane alkaloids

Aspidosperma alkaloids via cyclization of secodine intermediate: Synthesis of (±)-3-oxovincadifformine ethyl ester.

Abstract (±)-3-oxovincadifformine ethyl ester 14 has been synthesized through an intramolecular [4π+2π] cycloaddition of the 3-oxosecodine 13 first prepared in turn from the enamide 10 by dehydrogenation with benzeneseleninic anhydride. An insight into the conversion of 10 into 13 was gained, resulting in the suggestion of a plausible mechanistic pathway.

A highly enantioselective synthesis of (-)-antirhine by chemo-enzymatic approach

Abstract (−)-Antirhine 2 was synthesized in an efficient and stereocontrolled fashion from the readily available (1 R -2 S )-cyclohexene dimethanol monoacetate 6 . A key step was the regio- and stereoselective Pictet Spengler cyclization of the masked dialdehyde 12 to the indoloquinolizidinone 13 .

An efficient chemo-enzymatic approach to (+)-meroquinene

Abstract Meroquinene (+)- 1 was prepared in an efficient and stereocontrolled fashion from (1 R -2 S )-4-cyclohexene dimethanol monoacetate (−)- 8 . Key steps are the enzyme-catalyzed hydrolysis of the available diacetate 5 to (−)- 8 and of the intermediate diester 17 to hemiester 18 , which allow the stereo- and regiocontrolled elaboration of the vicinal vinyl and carboxymethyl groups.

1-Hydroxyrutaecarpine from Euxylophora paraënsis

Abstract The structure of the title compound has been determined on the basis of spectroscopic evidence and synthesis.

An Improved Procedure for the Synthesis of Oleuropeic Acid. I

Abstract 01 europeic acid 1, hexene-1-carboxylic acid (S)-(-)-4(1-hydroxy-1-methy1ethy1)-1-cyclo-,for which antiallegic properties have I recently been claimed, tive found in the root bark of the olive tree (Olea europea), is a naturally occurring-p-menthane derivative found in the root bark of the olive tree (Olea europea)2,3

Imine-enamine annelation: stereoselective syntheses of (±)-deplancheine

Abstract Two new approaches to synthesis of (±)-deplancheine (1) are described which utilize the alkylation of the imine-enamine (2) as the key ring-forming step.

1,2-Addition of dilithium trialkynylcuprates to αβ-unsaturated cyclic ketones

Selective 1,2-addition of alkynyl groups to cyclic αβ-unsaturated ketones may be effected by dilithium trialkynylcuprates in the presence of hexamethyl phosphoric triamide.

Indole alkaloids. A combined chemical and enzymatic route for eburnane ring construction : Formal synthesis of (−)-Eburnamonine

Abstract A stereocontrolled formal synthesis of (−)-eburnamonine 1, a tetracyclic indole alkaloid used as antihypertensive drug, has been achieve through the use of [3,3]-sigmatropic rearrangement (Claisen rearrangement) of the enantiopure β-alkoxy acrylate 4, available from rac-3-ethly-cyclohexenol 3 via lipase-catalyzed transesterification