136685-37-5Relevant articles and documents
Highly diastereoselective total syntheses of (+)-7-epigoniodiol, (-)-8-epigoniodiol, and (+)-9-deoxygoniopypyrone
Kumaraswamy, Gullapalli,Satish Kumar, Rangaraju
, p. 1366 - 1375 (2013/08/23)
An expedient concise total synthesis of (+)-7-epigoniodiol, (-)-8-epigoniodiol, and (+)-9-deoxygoniopypyrone is accomplished. The key transformations include a catalytic hydroxylation and base-mediated N-(acetyl)oxazolidinone addition reactions, which cou
Stereoselective total synthesis of bioactive styryllactones: 9-Deoxygoniopypyrone, goniopypyrone and 7-epi-goniofufurone
Prasad, Kavirayani R.,Dhaware, Madhuri G.
, p. 3697 - 3705 (2008/09/19)
Stereoselective synthesis of the bioactive styryllactones (+)-9-deoxygoniopypyrone, (+)-goniopypyrone and (+)-7-epi-goniofufurone has been achieved from D-(-)-tartaric acid. The key step involves the elaboration of a trihydroxy ester to the title compound
Facile stereoselective syntheses of goniodiol, 8-epi-goniodiol and 9-deoxygoniopypyrone
Prasad, Kavirayani R.,Gholap, Shivajirao L.
, p. 4679 - 4682 (2008/03/12)
Stereoselective syntheses of the bio-active styryllactones goniodiol and 9-deoxygoniopypyrone were accomplished from d-(-)-tartaric acid. The key step involves the elaboration of a γ-hydroxy butyramide to the styryllactones via high yielding stereoselecti
Efficient synthesis of the styryllactones, (+)-goniothalamin, (+)-7-epi-goniodiol and (+)-9-deoxygoniopypyrone
Liu, Zhi-Yu,Ji, Jian-Xin,Li, Bo-Gang
, p. 61 - 63 (2007/10/03)
An efficient synthesis of (+)-goniothalamin is described with aldehyde 4 as the key intermediate; the absolute configuration of (+)-7-epi-goniodiol was determined through its asymmetric synthesis from (+)-goniothalamin and, based on the conformation analysis of the four dihydroxylated isomers of (+)-goniothalamin, it can be concluded that the absolute configuration of the hydroxy at C8 determines the forms in nature.
Chiral hetero Diels-Alder products by enantioselective and diastereoselective zirconium catalysis. Scope, limitation, mechanism, and application to the concise synthesis of (+)-prelactone C and (+)-9-deoxygoniopypyrone
Yamashita, Yasuhiro,Saito, Susumu,Ishitani, Haruro,Kobayashi, Shu
, p. 3793 - 3798 (2007/10/03)
Catalytic asymmetric hetero Diels-Alder (HDA) reactions using a chiral zirconium complex have been developed. The reactions of aldehydes with Danishefsky's dienes proceeded smoothly to afford the corresponding pyranone derivatives in high yields with high diastereo- and enantioselectivities in the presence of a chiral zirconium complex, which was prepared from zirconium tert-butoxide, (R)-3,3′-diiodobinaphthol or its derivative, a primary alcohol, and a small amount of water. It is noted that 2,3-trans-pyranone derivatives were obtained with remarkably high diastereo- and enantioselectivities in the reaction with 4-methyl Danishefsky's diene. This is the first example of catalytic asymmetric trans-selective hetero Diels-Alder reactions of aldehydes. Furthermore, asymmetric HDA reactions with 4-benzyloxy Danishefsky's dienes were conducted to afford 2,3-cis-pyranone derivatives in high selectivities. Isolation of an intermediate of this asymmetric hetero Diels-Alder reaction indicated that the reaction proceeded in a stepwise cycloaddition pathway. Finally, these catalytic, asymmetric hetero Diels-Alder reactions were successfully applied to concise syntheses of biologically important natural pyranone derivatives, (+)-Prelactone C and (+)-9- deoxygoniopypyrone.
Stereoselective syntheses of (+)-goniodiol, (-)-8-epigoniodiol, and (+)-9-deoxygoniopypyrone via alkoxyallylboration and ring-closing metathesis
Ramachandran, P. Veeraraghavan,Chandra, J. Subash,Reddy, M. Venkat Ram
, p. 7547 - 7550 (2007/10/03)
A convenient synthesis of (+)-goniodiol, (-)-8-epigoniodiol, and (+)-9-deoxygoniopypyrone has been developed via asymmetric alkoxyallylboration and ring-closing metathesis pathways.
A short and general approach to the synthesis of styryllactones: (+)-Goniodiol, its acetates and β-trifluoromethyl derivative, (+)-7-epi-Goniodiol and (+)-9-deoxygoniopypyrone
Chen, Jian,Lin, Guo-Qiang,Wang, Zhi-Min,Liu, Han-Quan
, p. 1265 - 1268 (2007/10/03)
(+)-Goniodiol, its acetates and β-trifluoromethyl derivative, (+)-7-epi-Goniodiol and (+)-9-deoxygoniopypyrone, the representatives of styryllactones have been synthesized in a short and general way. The key steps involve the regioselective asymmetric dihydroxylation and the palladium-catalyzed cross-coupling of cyclic allylic carbonate with vinyltributylstannane.
Stereocontrolled syntheses of novel styryl lactones, (+)-goniodiol, (+)- goniotriol, (+)-8-acetylgoniotriol, (+)-goniofufurone, (+)-9- deoxygoniopypyrone, (+)-goniopypyrone, and (+)-altholactone from common intermediates and cytotoxicity of their congener
Tsubuki, Masayoshi,Kanai, Kazuo,Nagase, Hiromasa,Honda, Toshio
, p. 2493 - 2514 (2007/10/03)
Concise syntheses of (+)-goniodiol, (+)-goniotriol, (+)-8- acetylgoniotriol, (+)-goniofufurone, (+)-9-deoxygoniopypyrone, (+)- goniopypyrone, and (+)-altholactone and their congeners from chiral lactonic aldehydes 27 and 36 as common intermediates are des
Total synthesis of antitumor Goniothalamus styryllactones
Surivet, Jean-Philippe,Vatele, Jean-Michel
, p. 13011 - 13028 (2007/10/03)
Synthesis of eight enantiopure styryllactones has been achieved from a common precursor: ethyl (2S, 3S, 4R)-4-(t-butyldimethylsilyloxy)-2,3- isopropylidenedioxy-4-phenylbutanoate 16, prepared in five steps and 65% yield from (R)-mandelic acid. Key elements for the synthesis of goniofufurone 3, goniopypyrone 4, goniobutenolides A and B (5, 6) and 7-epi-goniofufurone 7 were the introduction of the Z-acrylate moiety by a Julia coupling between 16 or its epimer in benzylic position and methyl 3-phenylsulfonyl orthopropionate 11 followed by a highly diastereoselective reduction of the resulting β-keto sulfone which sets up the last of the four contiguous asymmetric center. In the case of styryllactones 4 and 7, prior to the Julia coupling, the benzyl sterocenter of 16 was efficiently inverted by a Mitsunobu reaction. Goniodiol 1 and 9-deoxygoniopypyrone 2 were synthesized via an efficient coupling between the primary triflate derived from the common intermediate 16 or its epimer and Ghosez's sulfone 11 followed by lactonization and PhSO2H elimination. Goniodiol 1 has been efficiently converted to another styryllactone: isogoniothalamin epoxide 41. Addition of the Ghosez's sulfone to an epoxide derived from the enantiomer of 16 allowed a short synthesis of 8-epi-9-deoxygoniopypyrone 8, thereby establishing that its structure is the following: (1R, 5R, 7S, 8S)-8-hydroxy-7-phenyl-2,6- dioxabicyclo[3.3.1] nonan-3-one.
A short and efficient total synthesis of the cytotoxic (+)-goniodiol and (+)-9-deoxygoniopypyrone
Surivet, Jean-Philippe,Vatele, Jean-Michel
, p. 7299 - 7300 (2007/10/03)
(+)-Goniodiol 7 and (+)-9-deoxygoniopypyrone 8, belonging to the group of styryllactones, have been synthesized in five steps and 75% yield respectively from C4-esters 1a and 1b. The key step of these syntheses is a triflate-sulfone coupling which allowed a rapid construction of the backbone of the title compounds as well as the efficient installation of a masked Z- acrylate moiety.
