122046-62-2Relevant academic research and scientific papers
Asymmetric synthesis of (-)-leiocarpin A via (-)-(S)-goniothalamin employing Julia-Kocienski olefination
Meruva, Suresh Babu,Raghavendra Rao,Mohammed, Aaseef,Dahanukar, Vilas H.,Kumar, U. K. Syam,Dubey
, p. 187 - 196 (2016)
A concise and enantioselective syntheses of antileukemic natural products such as (-)-(S)-goniothalamin and (-)-leiocarpin A has been accomplished in excellent yields. By employing reported conditions on suitable substrates via Julia-Kocienski olefination
Asymmetric synthesis of S-(+)-argentilactone and S-(-)-goniothalamin
Job,Wolberg,Müller,Enders
, p. 1796 - 1798 (2001)
The asymmetric synthesis of an α,β-unsaturated δ-lactone equivalent 8 as a key intermediate towards the total synthesis of a variety of natural products bearing such structural motifs is reported. An enzymatic approach was applied to provide both enantiomers of compound 8 using recLBADH (ee > 99%) and baker's yeast (ee = 94%), respectively. The utility of the intermediate was demonstrated by the total synthesis of the non-natural enantiomers of argentilactone [(S)-1] and goniothalamin [(S)-2].
Annulation-retro-Claisen cascade of bifunctional peroxides for the synthesis of lactone natural products
Hu, Lin,Li, Jialin,Li, Xuemin,Xu, Qianlan
supporting information, p. 274 - 277 (2022/01/03)
A new and highly efficient annulation-retro-Claisen cascade, which involves the [4 + 1] or [5 + 1] annulation of α-benzoylacetates with bielectrophilic peroxides and a subsequent debenzoylation process under mild basic conditions, has been developed for the rapid construction of valuable tetrahydrofuran- and dihydropyran-2-carboxylates in good yields. By employing the new reaction, the unified total synthesis of γ- and δ-lactone natural products such as (±)-tanikolide, (±)-goniothalamins, (±)-7-epi-goniodiol, and (±)-plakolide A has been accomplished in 4-7 steps.
Total Synthesis of (R)-Argentilactone and (R)-Goniothalamin Using a Free-Radical Photoredox Approach to α,β-Unsaturated δ-Lactones
Fuentes-Pantoja, Francisco J.,Cordero-Vargas, Alejandro
supporting information, p. 4433 - 4439 (2021/08/20)
α,β-Unsaturated δ-lactones are structural motifs found in diverse pharmacologically active natural products. In fact, the unsaturated lactone is often responsible for the biological activity. Herein, we report a new approach for the syntheses of (R)-argentilactone and (R)- goniothalamin based on a photoredox intermolecular iodolactonization mediated by a photoredox process. This new approach, already employed in our research group, stands as a new methodology to achieve several natural products containing α,β-Unsaturated δ-lactones.
An Alternative Approach to the Synthesis of Parvistone C
Addada, Ramakrishnam Raju,Regalla, Venkata Reddy,Gangireddy Venkata, Sivarami Reddy,Vema, Venkata Naresh,Anna, Venkateswara Rao
, p. 815 - 817 (2019/01/24)
A stereoselective total synthesis of parvistone C, an oxygenated natural styryllactone, has been accomplished in excellent overall yield by employing asymmetric aldol reaction, asymmetric epoxidation and regioselective epoxide ring opening as the key steps. Our synthetic strategy is very simple, concise and no use of protecting groups.
First total synthesis of the highly potent antitumor lactones 8-chlorogoniodiol and parvistone A: Exploiting a bioinspired late-stage epoxide ring-opening
Ramesh, Perla,Narasimha Reddy, Yarram,Narendar Reddy, Thatikonda,Srinivasu, Navuluri
supporting information, p. 246 - 249 (2017/02/15)
The first protecting group-free total syntheses of the highly potent antitumor chlorinated styryllactone secondary metabolites 8-chlorogoniodiol, parvistone A, and one analogue 8-epi-parvistone A, have been accomplished from commercially available trans-cinnamaldehyde in five steps with high overall yields. The chlorine-bearing stereogenic center of these silent secondary metabolites was introduced via a bioinspired late-stage regioselective epoxide ring-opening strategy. Maruoka asymmetric allylation, acrylation, ring-closing metathesis and asymmetric epoxidation, greatly facilitate the synthesis of the key intermediates goniothalamin oxide and (6S,7S,8S)-isogoniothalamin oxide.
Synthesis and cytotoxic activities of goniothalamins and derivatives
Weber, Anja,D?hl, Katja,Sachs, Julia,Nordschild, Anja C.M.,Schr?der, Dennis,Kulik, Andrea,Fischer, Thomas,Schmitt, Lutz,Teusch, Nicole,Pietruszka, J?rg
, p. 6115 - 6125 (2017/09/30)
Substituted goniothalamins containing cyclopropane-groups were efficiently prepared in high yields and good selectivity. Antiproliferative activity was measured on three human cancer cell lines (A549, MCF-7, HBL-100), to show which of the structural elements of goniothalamins is mandatory for cytotoxicity. We found that the configuration of the stereogenic centre of the δ-lactone plays an important role for cytotoxicity. In our studies only (R)-configured goniothalamins showed antiproliferative activity, whereby (R)-configuration accords to natural goniothalamin (R)-1. Additionally, the δ-lactone needs to be unsaturated whereas our results show that the vinylic double bond is not mandatory for cytotoxicity. Furthermore, with a two-fold in vitro and in vivo strategy, we determined the inhibitory effect of the compounds to the yeast protein Pdr5. Here, we clearly demonstrate that the configuration seems to be of minor influence, only, while the nature of the substituent of the phenyl ring is of prime importance.
Biosynthesis-Inspired Total Synthesis of Bioactive Styryllactones (+)-Goniodiol, (6S,7S,8S)-Goniodiol, (-)-Parvistone D, and (+)-Parvistone e
Ramesh, Perla,Rao, Tadikamalla P.
, p. 2060 - 2065 (2016/09/09)
A protecting-group-free total synthesis of (+)-goniodiol (1), (6S,7S,8S)-goniodiol (2), (-)-parvistone D (4), and (+)-parvistone E (6) was efficiently achieved in five steps from commercially available trans-cinnamaldehyde with high overall yields (72-75%). The synthesis strategy was inspired from the proposed biosynthesis pathway of styryllactones. Key transformations of the strategy include a one-pot conversion of goniothalamin oxide to goniodiol or 9-deoxygoniopypyrone in aqueous media, stereoselective epoxidation, ring-closing metathesis, and stereoselective Maruoka allylation. The route is amenable to synthesis of various analogues for biological evaluation.
Total synthesis of cryptomoscatone F1 through an asymmetric aldol approach
Ramesh, Perla,Raju, Atla,Fadnavis, Nitin W.
, p. 1251 - 1255 (2015/11/09)
A stereoselective total synthesis of naturally occurring styryl lactone, cryptomoscatone F1 is described. A Mukaiyama asymmetric aldol reaction, Brown's asymmetric allylation, Maruoka asymmetric allylation, and cross metathesis were used as the key steps.
Stereoselective synthesis of the non-lactonic portion of (Z)-cryptofolione and approaches towards its conversion to (Z)-cryptofolione
Nagendra, Siddavatam,Krishna Reddy, Vanka,Das, Biswanath
, p. 520 - 526 (2015/04/27)
The stereoselective synthesis of the non-lactonic part of the natural G2 checkpoint inhibitor, (Z)-cryptofolione, has been accomplished. Butane-1,4-diol was used as the starting material, and the stereogenic centers were generated through L-proline-catalyzed α-aminoxylation and Maruoka asymmetric allylation. We attempted to convert this non-lactonic moiety to (Z)-cryptofolione via olefin cross-metathesis reaction, but by this approach another naturally occurring lactonic compound, goniothalamin, was obtained.
