Asymmetric Synthesis of Styryl-Lactones

Abstract

A small, but extraordinary diverse class of bioactive styryl-lactones has been isolated from several species of the genus Goniothalamus (Annonnaceae). The interesting biological properties, in particular antitumoral, and structural diversity of these lactones have prompted several asymmetric syntheses. They may be classified in two types: synthesis from enantiomerically pure material (carbohydrate…) or with asymmetric methodologies (dihydroxylation, epoxidation…). This review will discuss the different strategies implemented to prepare these styryl-lactones.

Asymmetric Synthesis of (+)‐Altholactone: A Styryllactone Isolated from Various Goniothalamus Species

“…Purification by flash chromatography on silica gel (PE/Et 2 O 50:50) gave acetonide alcohol 12 (97 mg, 36 %) as a pale pink oil, together with recovered starting material 11 (160 mg, 59 %). 6,138.3,128.4,128.2,128.1,127.7,127.7,127.6,127.5,127.3, 3061, 3031, 2928, 2863, 1495, 1454, 1374, 1248, 1217, 1094, 880, 741, 2,6-Lutidine (120 mL, 1.03 mmol, 3.0 equiv) was added at 0 8C to a stirred solution of alcohol 12 (163 mg, 0.34 mmol, 1.0 equiv) in CH 2 Cl 2 (5 mL), followed by slow addition of TBSOTf (120 mL, 0.51 mmol, 1.5 equiv). The stirring was continued for 2 h at room temperature, after which the reaction was quenched with aqueous NH 4 Cl solution (10 mL).…”

“…[2,5] Because of the intriguing structures of the styryllactone family and their broad range of important biological activities, many synthetic methods to synthesise this core structure have been employed. [6] Most syntheses are based on the chiral pool concept, employing enantiopure starting materials such as carbohydrates, [7] glyceraldehyde, [8] hydroxy acids, [9] and amino acids. [10] Asymmetric syntheses [11] and chemoenzymatic approaches [12] are rather rare.…”

Novel (−)-goniofufurone mimics: Synthesis, antiproliferative activity and SAR analysis

“…After isolation of (+)-goniofufurone from the stem bark of Gonithalamus giganteus (Annonaceae) 1 in 1990, and the confirmation of the absolute stereochemistry of both 1 and ent-1, 2,3 many syntheses of these compounds with unique and intriguing structures have been published. [4][5][6][7][8][9][10][11][12][13][14][15][16][17][18] Both, 1 and ent-1, demonstrated a remarkable antiproliferative activity toward several human tumour cell lines. 19,20 Synthetic molecule 1 and some of its analogues showed more powerful cytotoxicity than the natural product ent-1 and the corresponding analogues from the (+)-series.…”

Regioselective Tandem Ring Closing/Cross Metathesis of 1,5‐Hexadien‐3‐ol Derivatives: Application to the Total Synthesis of Rugulactone

“…[1] They usually possess a styryl chain attached to the 6-position and have attracted the efforts of chemists over the past two decades. [2,3] Pyrones substituted by an allyl chain at this position have been more rarely isolated from nature. Among them, tuberolactone (2) identified as a trace in tuberose oil plays a major role in fragrance and flavor industries.…”