Norman L. Wendler

Total synthesis of the macrolide, zearalenone.

Abstract Total synthesis of the biologically active macrolide zearalenone together with its optical resolution and the determination of its absolute configuration as “S” are described. Wittig condensation with an ortho aldehydic ester proceeded in part with vicinal interaction and formation of an acetylenic product.

A total synthesis of griseofulvin and its optical antipode

Abstract An efficient total synthesis of (+) griseofulvin and its optical antipode, (−) griseofulvin, is described. Several aspects of the chemistry of this substance, its precursors and transformation products are discussed.

A stereoselective total synthesis of (±) prostaglandin E11,2

Abstract A stereoselective total synthesis of prostaglandin E1 employing 5-methoxyindanone-1 as starting material is described.

The total synthesis of (±) compactin and its natural (+) enantiomer

Abstract Total synthesis of (±) compactin 12 and its natural (+) enantiomer has been achieved via a multistep sequence originating from butadiene and p-benzoquinone.

Equilibrium relationship of D-homo ketolic systems

Abstract The ability of the various D-homo ketolic isomers arising from 17-hydroxy-20-keto steroids to equilibrate with each other under alkaline as well as Lewis acid conditions has been demonstrated and discussed.

The Faworskii rearrangement in the formation of 17-methyl steroids : The configuration of C-17 bromides

Abstract The configuration of 17-bromo-20-keto pregnanes and the 17-methyletianic esters have been determined. The Faworskii rearrangement of the former to give the latter has been observed to be abnormal. It is suggested that C-17 → C-21 halogen transfer intervenes.

A STEREOSELECTIVE TOTAL SYNTHESIS OF NAT(-)-PROSTAGLANDIN E(1) AND ITS OPTICAL ANTIPODE

Abstract A stereoselective total synthesis of nat (−) prostaglandin E 1 and its optical antipode employing the Diels-Alder adduct of trans -piperylene and maleic anhydride as starting material is described.

Group transfer and ring contraction phenomena in the d-homosteroid series

Abstract The d -homoketols arising from 17,21-dihydroxy-20-ketosteroids with aluminum alkoxides were observed to undergo alkaline catalyzed rearrangement with group transfer to yield diosphenols. The latter on more vigorous alkaline treatment suffered unidirectional benzilic acid ring contraction to afford 17β-hydroxyisoetianic acids. In the presence of formaldehyde and alkali, on the other hand, these same diosphenols were initially hydroxymethylated followed by ring-contraction to lactones.

A new route in the sequential total synthesis of compactin

Abstract The synthesis and regioselective hydrogenation of 1,2,6,7,8, 8aβ-hexahydro-8α-hydroxy-2-methylene-1β-naphthaleneacetic acid methyl ester 4a , has provided a novel synthetic pathway to the hypocholesterolemic agent, compactin 9 .

The relative configuration of flavipucine

Abstract The relative configuration of the antibiotic flavipucine as inferred from a differential rearrangement reaction was confirmed by ozonolysis to a crystalline oxidoester amide identical with a specimen of this same compound prepared by synthesis.